Pyrimidine compounds as herbicides

ABSTRACT

A method is disclosed for controlling the growth of undesired vegetation in a plantation crop by applying to the locus of the crop an effective amount of a compound of formula I ##STR1## and A, R 1 , R 2 , R 3 , R 4 , X, Y and Z are as defined in the disclosure. Also disclosed are novel substituted heterocyclic compounds and their agriculturally suitable compositions which are generally useful as herbicides, as well as methods of their use as general or selective preemergent or postemergent herbicides, or as plant growth regulants.

CROSS-REFERENCE TO RELATED APPLICATION

This application is 371 of PCT/US92/11330, filed Dec. 30, 1992, and published as WO93/14073 Jul. 22, 1993, and a continuation-in-part of application U.S. Ser. No. 07/821,118, filed Jan. 15, 1992, now abandoned.

FIELD OF THE INVENTION

This invention relates to novel substituted heterocyclic compounds and a method for controlling undesired vegetation in crops including plantation and specialty crops. Some of the compounds of the instant invention have been disclosed previously for use generally as herbicides, but these disclosures provide no teachings for use of these compounds as herbicides in plantation crops.

BACKGROUND OF THE INVENTION

U.S. Pat. No. 4,859,229 discloses herbicidal utility in "cotton and soya" cultivations for compounds of the formula ##STR2## wherein, inter alia R¹ is H, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, formyl or C₂ -C₆ alkanoyl;

R² is (in part) an ether group;

R³ is H or CN;

R⁴ is H or halogen;

R⁵ is H, halogen or C₁ -C₄ alkyl;

R⁶ is C₁ -C₄ alkyl or C₁ -C₄ haloalkyl; and

R⁵ and R⁶ together are tri- or tetramethylene.

The instant invention provides a method for controlling undesired vegetation in plantation and specialty crops. Many of the compounds of the instant invention have been previously disclosed for use generally as herbicides, and such disclosures are found in U.S. Pat. No. 4,859,229, EP-A-438,209, JP 3-77,874 and EP-A-408,382. There are, however, no teachings for the use of these compounds as herbicides in plantation and specialty crops such as citrus, sugarcane, coffee, banana, oil palm, loblolly pine, rubber, cocoa, grapes, plantain, pineapple, fruit trees such as apples, and nut trees. These crops are important markets and are cultivated particularly in regions of the Pacific rim and South America. Citrus, sugarcane and loblolly pine also are grown elsewhere.

The yields of selected crops such as citrus, sugarcane, coffee, banana, oil palm, loblolly pine, rubber, cocoa, grapes, fruit trees and Bermudagrass tend to be lessened by undesired plantings such as crabgrass, johnson grass, guineagrass and the like. In addition, the yields of these crops tend to be reduced by crop plants such as corn, cotton, wheat, rice, and the like. A need therefore exists for controlling these types of plantings to improve the yields of selected crops such as those mentioned above.

This invention also provides novel substituted heterocyclic compounds and their agriculturally suitable compositions which are generally useful as herbicides, as well as methods of their use as general or selective preemergent or postemergent herbicides, or as plant growth regulants.

New compounds effective for controlling the growth of undesired vegetation are in constant demand. In the most common situation, such compounds are sought to selectively control the growth of weeds in useful crops such as sugarcane, citrus, oil palm, cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around railroad tracks, storage tanks and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.

SUMMARY OF THE INVENTION

This invention comprises a method for controlling the growth of undesired vegetation in a plantation crop by applying to the locus of the crop an effective amount of a compound of Formula I ##STR3## A is O or S; R¹ is C₁ -C₄ alkyl optionally substituted with one or more halogen, OR⁵, SR⁶ or CN; C₃ -C₆ alkenyl or C₃ -C₆ alkynyl, each optionally substituted with 1-3 halogen; formyl; or C₂ -C₆ alkanoyl;

R² is H, isopropyl, allyl, propargyl, CH(CH₃)C≡CH, benzyl, CHR⁷ CO₂ R⁸ or may be taken together with Z;

R³ is C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or N(CH₃)₂ ;

R⁴ is H or halogen;

R³ and R⁴ may be taken together as --(CH₂)₃ -- or --(CH₂)₄ --;

R⁵ and R⁶ are independently H or C₁ -C₃ alkyl;

R⁷ and R⁸ are independently C₁ -C₂ alkyl;

X is Cl or Br;

Y is F or Cl;

Z is H or may be taken together with R² as ##STR4## such that the linking A atom is attached to the methine carbon; R⁹ is C₁ -C₃ alkyl, C₁ -C₃ haloalkyl, cyclopropyl, vinyl, C₂ alkynyl, CN, C(O)R¹⁰, CO₂ R¹⁰, CONR¹⁰ R¹¹, CR¹² R¹³ C(O)R¹⁰, CR¹² R¹³ CO₂ R¹⁰, CR¹² R¹³ CONR¹⁰ R¹¹, CHR¹² OH, CHR¹² OC(O)R¹⁰ or CHR¹² OC(O)NR¹⁰ R¹¹ ; and

R¹⁰, R¹¹, R¹² and R¹³ are independently H or C₁ -C₃ alkyl.

Preferred for reasons including greater herbicidal efficacy are:

1) The method wherein for Compounds of Formula I

R¹ is C₁ -C₃ alkyl optionally substituted with 1 to 3 F atoms or Cl atoms, O(C₁ -C₂ alkyl), S (C₁ -C₂ alkyl) or CN; C₃ -C₄ alkenyl optionally substituted with 1 to 3 F atoms or Cl atoms; C₃ -C₄ alkynyl; or C₂ -C₃ alkanoyl;

R² is H, isopropyl, allyl, propargyl, CH(CH₃)C≡CH, CHR⁷ CO₂ R⁸ or may be taken together with Z;

R³ is C₁ -C₂ alkyl, C₁ -C₂ haloalkyl or N(CH₃)₂ ;

R⁴ is H, F, Cl or Br;

R³ and R⁴ may be taken together as --(CH₂)₃ -- or --(CH₂)₄ --; and

X is Cl.

2) The method of Preferred 1 wherein

R¹ is CH₃ optionally substituted with 1 to 3 F atoms or Cl atoms; CH₂ CN; allyl; or propargyl;

R³ is CF₃ ; and

R⁴ is H.

3) The method of Preferred 2 wherein

R⁹ is CH₃ ;

A is O; and

Q is Q-1.

Specifically Preferred for reasons of greatest herbicidal efficacy are the method of Preferred 3 which are the use of the compounds:

3-[4-chloro-2-fluoro-5-[(2-propynyl)oxy]phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;

3-[4-chloro-2-fluoro-5-(2-propenyloxy)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;

3-(5,7-dichloro-2,3-dihydro-2-methyl-4-benzofuranyl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione; and

3-(7-choro-5-fluoro-2,3-dihydro-2-methyl-4-benzofuranyl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;

and the method of Preferred 2 which is the use of the compound:

3-[4-chloro-2-fluoro-5-[(2-propynyl)oxy]phenyl]-6-dimethylamino-1-methyl-1,3,5-triazine-2,4(1H,3H)-dione.

This invention also comprises compounds of Formulas II and III, agriculturally suitable compositions containing them, and their use as preemergent and/or postemergent herbicides. ##STR5## wherein A is O or S;

R¹ is C₁ -C₄ alkyl optionally substituted with one or more halogen, OR⁵, SR⁶ or CN; C₃ -C₆ alkenyl or C₃ -C₆ alkynyl, each optionally substituted with 1-3 halogens; formyl; or C₂ -C₆ alkanoyl;

R² is H, isopropyl, allyl, propargyl, CH(CH₃)C≡CH, benzyl, CHR⁷ CO₂ R⁸ or may be taken together with Z;

R³ is C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or N(CH₃)₂ ;

R⁴ is H or halogen;

R³ and R⁴ may be taken together as --(CH₂)₃ -- or --(CH₂)₄ --;

R⁵ and R⁶ are independently H or C₁ -C₃ alkyl;

R⁷ and R⁸ are independently C₁ -C₂ alkyl;

X is Cl or Br;

Y is F or Cl;

Z is H or may be taken together with R² as ##STR6##

such that the linking A atom is attached to the methine carbon; and

R⁹ is C₁ -C₃ alkyl, C₁ -C₃ haloalkyl, cyclopropyl, vinyl, C₂ alkynyl, CN, C(O)R¹⁰, CO₂ R¹⁰, CONR¹⁰ R¹¹, CR¹² R¹³ C(O)R¹⁰, CR¹² R¹³ CO₂ R¹⁰, CR¹² R¹³ CONR¹⁰ R¹¹, CHR¹² OH, CHR¹² OC(O)R¹⁰ or CHR¹² OC(O) NR¹⁰ R¹¹ ; and

R¹⁰, R¹¹, R¹² and R¹³ are independently H or C₁ -C₃ alkyl;

provided that

1) in compounds of Formula II, when R¹ is C₁ -C₄ alkyl optionally substituted with halogen, OR⁵ or CN; C₃ -C₄ alkenyl; formyl; or C₂ -C₆ alkanoyl; R³ is C₁ -C₄ haloalkyl; and R⁵ is C₁ -C₃ alkyl; then R² is benzyl or taken together with Z;

2) in compounds of Formula II, when R¹ is CH₂ OH or C₁ -C₃ alkyl optionally substituted with halogen; R³ is C₁ -C₄ haloalkyl; and A is S; then R² is taken together with Z;

3) in compounds of Formula III, when R¹ is C₁ -C₄ alkyl and R³ is CH₃ or CF₃ then R² is benzyl or taken together with Z;

4) in compounds of Formula II, when R¹ is C₁ -C₄ alkyl optionally substituted with halogen; formyl; or C₂ -C₆ alkanoyl; then R² is taken together with Z.

Preferred for reasons including ease of synthesis and/or greater herbicidal efficacy are:

1) Compounds of Formulas II and III wherein

R¹ is C₁ -C₃ alkyl optionally substituted with 1 to 3 F atoms or Cl atoms, O(C₁ -C₂ alkyl), S(C₁ -C₂ alkyl) or CN; C₃ -C₄ alkenyl optionally substituted with 1 to 3 F atoms or Cl atoms; C₃ -C₄ alkynyl; or C₂ -C₃ alkanoyl;

R² is H, isopropyl, allyl, propargyl, CH(CH₃)C≡CH, CHR⁷ CO₂ R⁸ or may be taken together with Z;

R³ is C₁ -C₂ alkyl, C₁ -C₂ haloalkyl or N(CH₃)₂ ;

R⁴ is H, F, Cl or Br;

R³ and R⁴ may be taken together as --(CH₂)₃ -- or --(CH₂)₄ --; and

X is Cl.

2) Compounds of Preferred 1 wherein

R¹ is CH₃ optionally substituted with 1 to 3 F atoms or Cl atoms; CH₂ CN; allyl; or propargyl;

R³ is CF₃ ; and

R₄ is H.

3) Compounds of Preferred 2 wherein the compound is of Formula II;

R⁹ is CH₃ ; and

A is O.

Specifically Preferred for reasons of ease of synthesis and/or greatest herbicidal efficacy are the compound of Preferred 2 which is:

3-[4-chloro-2-fluoro-5-[(2-propynyl)oxy]phenyl]-6-(dimethylamino-1-methyl-1,3,5-triazine-2,4(1H,3H) -dione;

and the compounds of Preferred 3 which are

3-(5,7-dichloro-2,3-dihydro-2-methyl-4-benzofuranyl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione; and

3-(7-choro-5-fluoro-2,3-dihydro-2-methyl-4-benzofuranyl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione.

In the above definitions, the term "alkyl", used either alone or in compound words such as "haloalkyl", includes straight chain or branched alkyl, e.g., methyl, ethyl, n-propyl, isopropyl or the different butyl isomers. Alkenyl includes straight chain or branched alkenes, e.g., 1-propenyl, 2-propenyl, 3-propenyl and the different butenyl isomers. The term "halogen", either alone or in compound words such as "haloalkyl", means fluorine, chlorine, bromine or iodine. Further, when used in compound words such as "haloalkyl" said alkyl may be partially or fully substituted with halogen atoms, which may be the same or different. Examples of haloalkyl include CH₂ CH₂ F, CF₂ CF₃ and CH₂ CHFCl.

DETAILED DESCRIPTION OF THE INVENTION

Many of the compounds of Formula I wherein Z and R² are not taken together can be prepared according to the procedures of U.S. Pat. No. 4,859,229 and U.S. Pat. No. 3,902,887, the disclosures of which are herein incorporated by reference.

Schemes 1 to 4 illustrate the preparation of compounds of Formula II wherein Z and R² are taken together. ##STR7##

The dihydrofuran ring of compounds of Formula II can be prepared according to the procedure of U.S. Pat. No. 4,881,967 by Claisen rearrangement of allyl ether VII followed by cyclization as shown in Scheme 1, Equations (c) and (d). The rearrangement and cyclization normally require high temperatures ranging from 100° C. to 200° C. Therefore, it is preferable to perform this process at an early stage with an inert protecting group on nitrogen. For this reason, phthalimide VII is prepared via treatment of hydroxyaniline V with phthalic anhydride IV followed by allylation of the hydroxy group of VI in the presence of a weak base such as potassium carbonate (Scheme 1, Equations (a) and (b)).

Alternatively, the compound VII can be prepared by allylation of V first followed by treatment with phthalic anhydride IV.

The rearrangement of VII can be effected by heating in an inert solvent such as N,N-dimethylaniline or o-dichlorobenzene at a temperature of about 100° C. to 200° C. This Claisen rearrangement can also proceed with titanium tetrachloride and N-trimethylsilylacetanilide at ambient temperature in an inert solvent such as dichloromethane (Narasaka, K., Bald E., and Mukaiyama T.; Chemistry Letters 1975, 1041). The cyclization of VIII to give IXa can be effected by refluxing a solution of phenol VIII in an inert solvent, such as xylene, containing a catalytic to stoichiometric amount of acid such as p-toluenesulfonic acid under Dean-Stark apparatus at a temperature range of from about 120° C. to 180° C. (Scheme 1, Equation (d)). ##STR8##

For the preparation of dihydrothiophene IXb, the allylphenol VIII is treated with N,N-dimethylthiocarbamoyl chloride in the presence of a weak base such as potassium carbonate in an inert solvent such as acetone or N,N-dimethylformamide at a temperature between 0° C. and refluxing temperatures of the solvents over several hours as shown in Scheme 2a, Equation (a).

Thermal rearrangement of X may be effected in a suitable inert solvent such as o-dichlorobenzene at 150°-250° C. to produce carbamate derivative XI. Cyclization of XI with an anhydrous acid such as hydrogen bromide in acetic acid at refluxing temperatures affords IXb as shown in Scheme 2a, Equation (c).

The acetylene substituted dihydrofuran ring of compounds of Formulas II and III (i.e., R⁹ is C₂ alkynyl) can be prepared as shown in Scheme 2b. ##STR9##

The hydroxyl group of VIII of Scheme 1, Equation (c) can be protected by a silicon protecting group using reagents such as trimethylsilyl chloride or t-butyldimethylsilyl chloride to give XXXIV. Then the reductive ozonolysis of XXXIV gives aldehyde XXXV. The diol XXXVI can be prepared by the treatment of aldehyde XXXV with lithium salt of trimethylsilylacetylene. The deprotections of both silyl protecting groups of XXXVI can be accomplished using fluoride ions such as potassium fluoride. The acetylenic hydrofuran XXXVIII can be prepared from the diol XXXVII by Mitsunobu condition using diethyl azodicarboxylate (DEAD) and triphenylphosphine according to the known procedure (Macor, J., Ryan, K., and Newman, M.; Tetrahedron 1992, 48, 1039).

The vinyl group substituted dihydrofuran ring of compounds of Formula II and III can be prepared as shown in Scheme 2c. ##STR10##

The hydroxymethyl hydrofuran XXXIX can be prepared by treatment of VIII with m-chloroperbenzoic acid (MCPBA) followed by p-toluenesulfonic acid. The treatment of XXXIX with carbon tetrabromide and triphenylphosphine gives bromomethyl hydrofuran XL. The Wittig reagent XLI can be prepared by the treatment of XL with triphenylghosphine in an inert solvent such as DMF. The vinylic hydrofuran XLII can be prepared by Wittig reaction of XLI and formaldehyde.

The hydroxy group of XXXIX can be converted to ketone, carboxylic acid, ester or amide groups by methods well known to those skilled in the art. This transformation can be carried out before or after the phthalimide protecting group is removed. If the protecting group is removed first, then the unprotected aniline derivative is first converted to the uracil or triazinedione ring (as described later) before further conversion of the hydroxyl group. ##STR11##

The phthalimide protecting group of IXa or IXb can be removed by hydrazine at ambient temperature to afford aniline XII. The formation of isocyanate XIII is accomplished by treatment of the aniline XII with phosgene or triphosgene in the presence of a base such as triethylamine at ambient temperature, or without base in an inert solvent such as dioxane or toluene at a temperature range of from 60° C. to 120° C. (Scheme 3). ##STR12##

The formation of the uracil ring in compound XV is carried out by the procedure described in U.S. Pat. No. 4,943,309. A suitable salt of an enamine XIV is treated with the isocyanate XIII at low temperature over several hours, typically between -50° C. and -70° C. in an inert solvent such as toluene, and the reaction is continued at ambient temperature for several hours. The alkylation of XV can be accomplished by treatment of XV with C₁₋₄ alkyl halide, or C₁₋₄ haloalkyl halide, especially the respective chloride or bromide, or sulphate in the presence of a base such as potassium carbonate or sodium hydride in an inert solvent such as acetone or acetonitrile at a temperature range of from about 0° C. to 120° C. The acylation of XV is carried out with acetic anhydride or a C₂₋₆ alkanecarboxylic acid halide, in the presence of base such as sodium hydride.

Schemes 5 and 6 illustrate the preparation of compounds of Formula III. ##STR13##

The formation of the triazinedione ring follows the procedure described in U.S. Pat. No. 3,902,887 when R³ is a dimethylamino group as shown in Scheme 5. N-Ethoxycarbonylguanidine XVI is mixed with an isocyanate XVII in an inert solvent, preferably toluene, while the temperature is maintained at 25° C. to 100° C., preferably 55° C. to 80° C. The mixture of slurry containing compound XVIII is cooled, if necessary, to 24° C.-45° C., while dimethylamine is added, either as a gas or a liquid. It is preferred to add the amine at 25° C.-35° C., and it is important to have at least 1.0 molar equivalent and preferably, 1.0 to 2.5 molar equivalents of dimethylamine. Next a ring closure catalyst is added. The catalyst is an alkali metal alkoxide (or hydroxide) and it may be added either as a dry solid or as a solution in the alkanol. Dry sodium methoxide or a solution of sodium methoxide in methanol is a preferred catalyst. The amount of catalyst needed is from 0.1 to 5.0 mole percent of compound XVIII. The ring closure reaction can proceed at a temperature between 0° C. and 120° C. The reaction is rapid and normally complete in less than several hours. ##STR14##

When R³ is C₁ -C₄ alkyl and C₁ -C₄ haloalkyl substituents, the formation of the triazinedione ring follows the procedure described by JP 03 77,874 as shown in Scheme 6. Carbamoylation of alkylamidine hydrochloride or haloalkylamidine hydrochloride XIX with isocyanate XVII under the condition described in Scheme 5 or in the presence of NaOH in aqueous acetone gives N-phenylcarbamoyl amidine XX. The cyclocondensation of the resulting compound XX with ethyl chloroformate in the presence of base such as sodium hydride or sodium methoxide in an inert solvent such as tetrahydrofuran gives triazinedione XXII via XXI. The alkylation of XXII can be accomplished by treatment of XXII with C₁₋₄ alkyl halide, or C₁ -C₄ haloalkyl halide, especially the respective chloride, bromide or sulphate in the presence of a base such as potassium carbonate or sodium hydride in an inert solvent such as acetone or acetonitrile at a temperature range of from about 0° C. to 120° C. The acylation of XXII is carried out with acetic anhydride or a C₂ -C₆ alkanecarboxylic acid halide in the presence of base such as sodium hydride. ##STR15##

Compounds of Formula II wherein Z is hydrogen and A is oxygen can be prepared according to Scheme 7. Cyclocondensation of enamine XIV can be carried out with benzyl ether protected isocyanate XXIII. The enamine XIV wherein R³ and R⁴ are taken together as --(CH₂)₃ -- or --(CH₂)₄ -- can be prepared according to the known procedure (Kloek, J., and Leschinsky, K.; J. Org Chem., 1978, 43, 1460). Other enamines of Formula XIV wherein R³ and R⁴ are not taken together can be prepared by one skilled in the art. The resultant uracil XXIV is alkylated or acylated as described previously and benzyl ether XXV can be deprotected easily with 5 to 10% palladium on charcoal under hydrogen pressure ranging from 20 to 50 psi. The resulting phenol XXVI is treated with C₁ -C₄ alkyl halide, or C₁ -C₄ haloalkyl halide, especially the respective chloride or bromide in the presence of a base such as potassium carbonate or sodium hydride in an inert solvent such as acetone or acetonitrile at a temperature range of from about 0° C. to 120° C. to give XXVII. ##STR16##

The compound XXX which has two identical R¹⁰ substituents (wherein R¹⁰ is isopropyl, allyl or C₃ -C₄ alkynyl) can be prepared by deprotection of benzyl ether XXIV with palladium on charcoal under hydrogen followed by alkylation or acylation in the presence of base as shown in Scheme 8. ##STR17##

The same procedure can be adopted for the synthesis of triazinediones of Formula III wherein Z is hydrogen and A is oxygen as shown in Scheme 9. The cyclocondensation product XXXI from N-ethoxycarbonylguanidine XVI and benzyl ether protected isocyanate XXIII is treated with palladium on charcoal under hydrogen pressure ranging from 20 to 50 psi followed by alkylation or acylation in the presence of base to give XXXIII.

EXAMPLE 1

Preparation of 3-[4-chloro-2-fluoro-5-[(2-propynyl)-oxy]phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H, 3H)-pyrimidinedione

To a solution of 200 mg (0.59 mmol) of 3-[4-chloro-2-fluoro-5-(hydroxy)phenyl]-1-methyl-6- (trifluoromethyl)-2,4 (1H,3H) -pyrimidinedione in 3 mL of acetonitrile was added 162 mg of potassium carbonate (1.18 mmol) and 131 mL (1.18 mmol) of an 80% solution of propargyl bromide in toluene. It was warmed under reflux for 2 h. The resulting mixture was filtered and the filtrate was concentrated in vacuo to give colorless oil which was flash chromatographed over silica gel, eluting with a 1:4 v:v mixture of ethyl acetate and hexane to give 204 mg of title compound as a white foam: ¹ H-NMR (CDCl₃, 200 MHz) ppm 7.35 (d, 1H), 7.0 (d, 1H), 6.4 (s, 1H), 4.78 (d, 2H), 3.58 (s, 3H), 2.6 (d, 1H).

EXAMPLE 2

Preparation of 3-[4-chloro-2-fluoro-5-(hydroxy)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H, 3H) -pyrimidinedione

A mixture of 1.12 g (2.61 mmol) of 3-[4-chloro-2-fluoro-5-(phenylmethoxy)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione and 220 mg of 10% palladium on charcoal in 40 mL of ethyl acetate was placed in a Paar bottle and was agitated under 45 psi hydrogen over a 20 hour period. It was filtered and washed with 100 mL of ethyl acetate. The filtrate was concentrated in vacuo and the resultant crude product flash chromatographed over silica gel eluting with a 1:4 v:v mixture of ethyl acetate and hexane to give 521 mg of the title compound as a white foam.: ¹ H-NMR (CDCl₃, 200 MHz) ppm 7.15 (d, 1H) , 6.9 (d, 1H) , 6.4 (s, 1H), 5.8 (s, 1H), 3.6 (s, 3H).

EXAMPLE 3

Preparation of 3-[4-chloro-2-fluoro-5-(phenylmethoxy)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione

A mixture of 1.85 g (4.46 mmol) of 3-[4-chloro-2-fluoro-5-(phenylmethoxy)phenyl]-6-(trifluoromethyl)-2,4(1H, 3H)-pyrimidinedione, 492 μL (5.20 mmol) of dimethylsulfate, and 749 mg (8.92 mmol) of sodium bicarbonate in 20 mL of acetone was warmed under reflux for 3 h. Evaporation removed the solvent to give a viscous residue. It was dissolved in 50 mL of ether and washed twice with 30 mL of water, dried (MgSO₄) and concentrated in vacuo to give white solid which was flash chromatographed over silica gel, eluting with a 1:4 v:v mixture of ethyl acetate and hexane to give 1.19 g of the title compound as a white solid, m.p.: 145°-147° C.; ¹ H-NMR (CDCl₃, 200 MHz) ppm 7.4 (m, 6H), 6.85 (d, 1H), 6.4 (s, 1H), 5.1 (s, 2H), 3.55 (s, 3H).

EXAMPLE 4

Preparation of 3-[4-chloro-2-fluoro-5-(phenylmethoxy)-phenyl]-6-(trifluoromethyl)-2,4(1H,3H) -pyrimidinedione

To a solution of 312 mg (7.82 mmol) of sodium hydride (60% oil dispersion) in 10 mL of N,N-dimethylformamide was added 1.43 g (7.82 mmol) of ethyl-3-amino-4,4,4-trifluorocrotonate in 7 mL of toluene over a period of 30 min at -5° C. The resulting mixture was stirred for an additional 30 min before it was cooled to -70° C. Then a solution of 2.17 g (7.82 mmol) of 4-chloro-2-fluoro-5-(phenylmethoxy)phenyl isocyanate in 7 mL of toluene was added dropwise at a rate that maintained the reaction temperature below -60° C. After the addition, the thick reaction mixture was maintained at -60° C. for an additional 1 h before the cooling bath was removed. The mixture was gradually warmed to room temperature and stirring was continued for 1.5 h. Then the mixture was poured into a solution of 10 mL of concentrated HCl in 200 mL of water. The toluene layer was separated and the aqueous layer was further extracted twice with 200 mL of ether, dried (MgSO₄), concentrated in vacuo to give yellow oil which was flash chromatographed over silica gel eluting with a 1:4 v:v mixture of ethyl acetate and hexane to give 1.85 g of the title compound as a pale yellow foam: ¹ H-NMR (CDCl₃, 200 MHz): ppm 7.40 (m, 6H), 6.85 (d, 1H), 6.2 (s, 1H), 5.05 (s, 2H).

EXAMPLE 5

Preparation of 3-[4-chloro-2-fluoro-5-[(2-propynyl)-oxy]phenyl]-1-(2-propynyl)-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione

To a stirred solution of 500 mg (1.50 mmol) of 3-[4 -chloro-2-fluoro-5-(hydroxy)phenyl]-6-trifluoromethyl-2,4(1H,3H) -pyrimidinedione in 20 mL of acetonitrile was added 425 mg (3.1 mmol) of potassium carbonate and 0.34 mL (3.10 mmol) of 80% solution of propargyl bromide in toluene. The stirred mixture was then refluxed gently under nitrogen for 2 h. The solution was filtered, washed with ethyl acetate, and concentrated in vacuo. The resulting yellow oil was flash chromatographed over silica gel, eluting with a 1:4 v:v mixture of ethyl acetate and hexane to give 90 mg of the title compound as a pale yellow oil: ¹ H-NMR (CDCl₃, 200 MHz): ppm 7.35 (d, 1H), 7.0 (d, 1H), 6.4 (s, 1H), 4.75 (m, 4H), 2.6 (m, 1H), 2.4 (m, 1H). It also gives 150 mg of 3-[4-chloro-2-fluoro-5-[(2-propynyl) oxy]phenyl]-1-6-(trifluoromethyl)-2,4 (1H,3H)-pyrimidinedione as a yellow oil: ¹ H-NMR (DMSO-d₆): ppm 7.7 (d, 1 H), 7.4 (d, 1H), 6.4 (s, 1H), 4.8 (d, 2H), 2.5 (m, 1H).

EXAMPLE 6

Preparation of 3-[4-chloro-2-fluoro-5-(hydroxy)phenyl]-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

A mixture of 4.27 g (10.3 mmol) of 3-[4-chloro-2-fluoro-5-(phenylmethoxy)phenyl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione and 420 mg of 10% palladium on charcoal in 70 mL of ethyl acetate was placed in a Paar bottle and was agitated under 45 psi hydrogen over a 16 hour period. It was filtered and washed with ethyl acetate. The filtrate was concentrated in vacuo and the resultant crude product flash chromatographed over silica gel, eluting with a 95:5 v:v mixture of dichloromethane and methanol to give 2.50 g of the title compound as a pale orange solid, m.p.: 68°-72° C.; ¹ H-NMR (DMSO-d₆): ppm 7.5 (d, 1H), 7.0 (d, 1H), 6.4 (s, 1H).

EXAMPLE 7

Preparation of 3-[4-chloro-2-fluoro-5-[(2-propynyl)-oxy]phenyl]-6-(dimethylamino)-1-methyl-1,3,5-triazine-2,4(1H,3H)-dione

To a solution of 2.80 g (8.90 mmol) of 3-[4-chloro-2-fluoro-5-(hydroxy)phenyl]-6-(dimethylamino)-1-methyl-1,3,5-triazine-2,4(1H,3H) -dione in 50 mL of acetone was added 1.47 g (10.7 mmol) of potassium carbonate and 1.98 mL (17.8 mmol) of an 80% solution of propargyl bromide in toluene. It was then warmed to reflux for 2 h. It was cooled to room temperature and the mixture was filtered and washed with excess ethyl acetate. The crude product was flash chromatographed over silica gel, eluting with a 3:7 v:v mixture of ethyl acetate and hexane to give 3.1 g of the title compound as a pale yellow solid, m.p.: 61°-65° C.; ¹ H-NMR (CDCl₃, 200 MHz) ppm 7.0 (d, 1H), 4.75 (m, 2H), 3.45 (s, 3H), 3.1 (s, 6H), 2.6 (m, 1H).

EXAMPLE 8

Preparation of 3-[4-chloro-2-fluoro-5-(hydroxy)phenyl]-6-(dimethylamino)-1-methyl-1,3,5-triazine-2,4(1H,3H)-dione

A mixture of 4.62 g (11.4 mmol) of 3-[4-chloro-2-fluoro-5-(phenylmethoxy)phenyl]-6-(dimethylamino)-1-methyl-1,3,5-triazine-2,4(1H,3H)-dione and 460 mg of 10% palladium on charcoal in 50 mL of ethyl acetate was placed in a Paar bottle and was agitated under 45 psi hydrogen over a 14 hour period. It was filtered and washed with ethyl acetate. The filtrate was concentrated in vacuo and the resultant crude product flash chromatographed over silica gel eluting with a 1:1 v:v mixture of ethyl acetate and hexane to give 3.2 g of the title compound as a pale grey solid, m.p.: 247°-249° C. (dec); ¹ H-NMR (DMSO-d₆) ppm 7.45 (d, 1H), 6.95 (d, 1H), 3.3 (s, 3H), 3.0 (s, 6H).

EXAMPLE 9

Preparation of 3-[4-chloro-2-fluoro-5-(phenylmethoxy)-phenyl]-6-(dimethylamino)-1-methyl-1,3,5-triazine-2,4(1H,3H)-dione

To a solution of 5.05 g (29.2 mmol) of N-ethoxycarbonyl-N,N', N"-trimethylguanidine in 25 mL of toluene was added a solution of 7.72 g (27.8 mmol) of 4-chloro-2-fluoro-5-(phenylmethoxy)phenyl isocyanate in 50 mL of toluene over a period of 30 min while maintaining the temperature between 55° C. and 80° C. It was then stirred at the same temperature for an hour. To a solution of the resulting N-[N-[4-chloro-2-fluoro-5-(phenylmethoxy) phenyl]carbamoyl-N',N'-dimethylamidino]-N-methylcarbamate in toluene was added 3.21 g (71.5 mmol) of dimethylamine in 10 mL of toluene at room temperature. While the temperature was between 25° C. and 40° C., 45 mg (0.834 mmol) of sodium methoxide was added. After 30 min, it was quenched with 100 mL of water. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with 0.1N hydrochloric acid, brine, and water, dried (MgSO₄) and concentrated in vacuo. The crude product was flash chromatographed over silica gel eluting with a 1:1 v:v mixture of ethyl acetate and hexane to give 5.3 g of the title compound as a brown solid, m.p.: 193°-194° C.; ¹ H-NMR (CDCl₃, 200 MHZ) ppm 7.4 (m, 6H), 6.95 (d, 1H), 5.05 (d, 2H), 3.45 (s, 3H), 3.1 (s, 6H).

Using the procedures outlined in Schemes 1-9, and Examples 1-9, the compounds of this invention including the compounds of Tables I-III can readily be prepared by one skilled in the art.

                  TABLE I                                                          ______________________________________                                          ##STR18##                                                                     R.sup.1    R.sup.2     R.sup.3   R.sup.4                                                                            A   X   Y                                 ______________________________________                                         CH.sub.3   H           CF.sub.3  H   O   Cl  F                                 CH.sub.3   H           CF.sub.3  H   S   Cl  F                                 CH.sub.3   H           CF.sub.3  H   O   Cl  Cl                                CH.sub.3   H           CF.sub.3  H   S   Cl  Cl                                CH.sub.3   H           CF.sub.3  Br  O   Cl  F                                 CH.sub.3   H           CF.sub.3  Br  S   Cl  F                                 CH.sub.3   H           CF.sub.3  Br  O   Cl  Cl                                CH.sub.3   H           CF.sub.3  Br  S   Cl  Cl                                CH.sub.3   CH.sub.2 Ph CF.sub.3  H   O   Cl  F                                 CH.sub.3   CH.sub.2 Ph CF.sub.3  H   S   Cl  F                                 CH.sub.3   CH.sub.2 Ph CF.sub.3  H   O   Cl  Cl                                CH.sub.3   CH.sub.2 Ph CF.sub.3  H   S   Cl  Cl                                CH.sub.3   CH.sub.2 Ph CF.sub.3  Br  O   Cl  F                                 CH.sub.3   CH.sub.2 Ph CF.sub.3  Br  S   Cl  F                                 CH.sub.3   CH.sub.2 Ph CF.sub.3  Br  O   Cl  Cl                                CH.sub.3   CH.sub.2 Ph CF.sub.3  Br  S   Cl  Cl                                CH.sub.3                                                                                   ##STR19##  CF.sub.3  H   O   Cl  F                                 CH.sub.3                                                                                   ##STR20##  CF.sub.3  H   S   Cl  F                                 CH.sub.3                                                                                   ##STR21##  CF.sub.3  H   O   Cl  Cl                                CH.sub.3                                                                                   ##STR22##  CF.sub.3  H   S   Cl  Cl                                CH.sub.3                                                                                   ##STR23##  CF.sub.3  Br  O   Cl  F                                 CH.sub.3                                                                                   ##STR24##  CF.sub.3  Br  S   Cl  F                                 CH.sub.3                                                                                   ##STR25##  CF.sub.3  Br  O   Cl  Cl                                CH.sub.3                                                                                   ##STR26##  CF.sub.3  Br  S   Cl  Cl                                CH.sub.3   iPr         CF.sub.3  H   O   Cl  F                                 CH.sub.3   iPr         CF.sub.3  H   S   Cl  F                                 CH.sub.3   iPr         CF.sub.3  H   O   Cl  Cl                                CH.sub.3   iPr         CF.sub.3  H   S   Cl  Cl                                CH.sub.3   iPr         CF.sub.3  Br  O   Cl  F                                 CH.sub.3   iPr         CF.sub.3  Br  S   Cl  F                                 CH.sub.3   iPr         CF.sub.3  Br  O   Cl  Cl                                CH.sub.3   iPr         CF.sub.3  Br  S   Cl  Cl                                CH.sub.3   CH.sub.2 CCH.sub.2                                                                         CF.sub.3  H   O   Cl  F                                 CH.sub.3   CH.sub.2 CCH.sub.2                                                                         CF.sub.3  H   S   Cl  F                                 CH.sub.3   CH.sub.2 CCH.sub.2                                                                         CF.sub.3  H   O   Cl  Cl                                CH.sub.3   CH.sub.2 CCH.sub.2                                                                         CF.sub.3  H   S   Cl  Cl                                CH.sub.3   CH.sub.2 CCH.sub.2                                                                         CF.sub.3  Br  O   Cl  F                                 CH.sub.3   CH.sub.2 CCH.sub.2                                                                         CF.sub.3  Br  S   Cl  F                                 CH.sub.3   CH.sub.2 CCH.sub.2                                                                         CF.sub.3  Br  O   Cl  Cl                                CH.sub.3   CH.sub.2 CCH.sub.2                                                                         CF.sub.3  Br  S   Cl  Cl                                CF.sub.3   H           CF.sub.3  H   O   Cl  F                                 CF.sub.3   H           CF.sub.3  H   S   Cl  F                                 CF.sub.3   H           CF.sub.3  H   O   Cl  Cl                                CF.sub.3   H           CF.sub.3  H   S   Cl  Cl                                CF.sub.3   H           CF.sub.3  Br  O   Cl  F                                 CF.sub.3   H           CF.sub.3  Br  S   Cl  F                                 CF.sub.3   H           CF.sub.3  Br  O   Cl  Cl                                CF.sub.3   H           CF.sub.3  Br  S   Cl  Cl                                CF.sub.3   CH.sub.2 Ph CF.sub.3  H   O   Cl  F                                 CF.sub.3   CH.sub.2 Ph CF.sub.3  H   S   Cl  F                                 CF.sub.3   CH.sub.2 Ph CF.sub.3  H   O   Cl  Cl                                CF.sub.3   CH.sub.2 Ph CF.sub.3  H   S   Cl  Cl                                CF.sub.3   CH.sub.2 Ph CF.sub.3  Br  O   Cl  F                                 CF.sub.3   CH.sub.2 Ph CF.sub.3  Br  S   Cl  F                                 CF.sub.3   CH.sub.2 Ph CF.sub.3  Br  O   Cl  Cl                                CF.sub.3   CH.sub.2 Ph CF.sub.3  Br  S   Cl  Cl                                CF.sub.3                                                                                   ##STR27##  CF.sub.3  H   O   Cl  F                                 CF.sub.3                                                                                   ##STR28##  CF.sub.3  H   S   Cl  F                                 CF.sub.3                                                                                   ##STR29##  CF.sub.3  H   O   Cl  Cl                                CF.sub.3                                                                                   ##STR30##  CF.sub.3  H   S   Cl  Cl                                CF.sub.3                                                                                   ##STR31##  CF.sub.3  Br  O   Cl  F                                 CF.sub.3                                                                                   ##STR32##  CF.sub.3  Br  S   Cl  F                                 CF.sub.3                                                                                   ##STR33##  CF.sub.3  Br  O   Cl  Cl                                CF.sub.3                                                                                   ##STR34##  CF.sub.3  Br  S   Cl  Cl                                CF.sub.3   iPr         CF.sub.3  H   O   Cl  F                                 CF.sub.3   iPr         CF.sub.3  H   S   Cl  F                                 CF.sub.3   iPr         CF.sub.3  H   O   Cl  Cl                                CF.sub.3   iPr         CF.sub.3  H   S   Cl  Cl                                CF.sub.3   iPr         CF.sub.3  Br  O   Cl  F                                 CF.sub.3   iPr         CF.sub.3  Br  S   Cl  F                                 CF.sub.3   iPr         CF.sub.3  Br  O   Cl  Cl                                CF.sub.3   iPr         CF.sub.3  Br  S   Cl  Cl                                CF.sub.3   CH.sub.2 CCH.sub.2                                                                         CF.sub.3  H   O   Cl  F                                 CF.sub.3   CH.sub.2 CCH.sub.2                                                                         CF.sub.3  H   S   Cl  F                                 CF.sub.3   CH.sub.2 CCH.sub.2                                                                         CF.sub.3  H   O   Cl  Cl                                CF.sub.3   CH.sub.2 CCH.sub.2                                                                         CF.sub.3  H   S   Cl  Cl                                CF.sub.3   CH.sub.2 CCH.sub.2                                                                         CF.sub.3  Br  O   Cl  F                                 CF.sub.3   CH.sub.2 CCH.sub.2                                                                         CF.sub.3  Br  S   Cl  F                                 CF.sub.3   CH.sub.2 CCH.sub.2                                                                         CF.sub.3  Br  O   Cl  Cl                                CF.sub.3   CH.sub.2 CCH.sub.2                                                                         CF.sub.3  Br  S   Cl  Cl                                 ##STR35## H           CF.sub.3  H   O   Cl  F                                  ##STR36## H           CF.sub.3  H   S   Cl  F                                  ##STR37## H           CF.sub.3  H   O   Cl  Cl                                 ##STR38## H           CF.sub.3  H   S   Cl  Cl                                 ##STR39## H           CF.sub.3  Br  O   Cl  F                                  ##STR40## H           CF.sub.3  Br  S   Cl  F                                  ##STR41## H           CF.sub.3  Br  O   Cl  Cl                                 ##STR42## H           CF.sub.3  Br  S   Cl  Cl                                 ##STR43## CH.sub.2 Ph CF.sub.3  H   O   Cl  F                                  ##STR44## CH.sub.2 Ph CF.sub.3  H   S   Cl  F                                  ##STR45## CH.sub.2 Ph CF.sub.3  H   O   Cl  Cl                                 ##STR46## CH.sub.2 Ph CF.sub.3  H   S   Cl  Cl                                 ##STR47## CH.sub.2 Ph CF.sub.3  Br  O   Cl  F                                  ##STR48## CH.sub.2 Ph CF.sub.3  Br  S   Cl  F                                  ##STR49## CH.sub.2 Ph CF.sub.3  Br  O   Cl  Cl                                 ##STR50## CH.sub.2 Ph CF.sub.3  Br  S   Cl  Cl                                 ##STR51##                                                                                 ##STR52##  CF.sub.3  H   O   Cl  F                                  ##STR53##                                                                                 ##STR54##  CF.sub.3  H   S   Cl  F                                  ##STR55##                                                                                 ##STR56##  CF.sub.3  H   O   Cl  Cl                                 ##STR57##                                                                                 ##STR58##  CF.sub.3  H   S   Cl  Cl                                 ##STR59##                                                                                 ##STR60##  CF.sub.3  Br  O   Cl  F                                  ##STR61##                                                                                 ##STR62##  CF.sub.3  Br  S   Cl  F                                  ##STR63##                                                                                 ##STR64##  CF.sub.3  Br  O   Cl  Cl                                 ##STR65##                                                                                 ##STR66##  CF.sub.3  Br  S   Cl  Cl                                 ##STR67## iPr         CF.sub.3  H   O   Cl  F                                  ##STR68## iPr         CF.sub.3  H   S   Cl  F                                  ##STR69## iPr         CF.sub.3  H   O   Cl  Cl                                 ##STR70## iPr         CF.sub.3  H   S   Cl  Cl                                 ##STR71## iPr         CF.sub.3  Br  O   Cl  F                                  ##STR72## iPr         CF.sub.3  Br  S   Cl  F                                  ##STR73## iPr         CF.sub.3  Br  O   Cl  Cl                                 ##STR74## iPr         CF.sub.3  Br  S   Cl  Cl                                 ##STR75## CH.sub.2 CCH.sub.2                                                                         CF.sub.3  H   O   Cl  F                                  ##STR76## CH.sub.2 CCH.sub.2                                                                         CF.sub.3  H   S   Cl  F                                  ##STR77## CH.sub.2 CCH.sub.2                                                                         CF.sub.3  H   O   Cl  Cl                                 ##STR78## CH.sub.2 CCH.sub.2                                                                         CF.sub.3  H   S   Cl  Cl                                 ##STR79## CH.sub.2 CCH.sub.2                                                                         CF.sub.3  Br  O   Cl  F                                  ##STR80## CH.sub.2 CCH.sub.2                                                                         CF.sub.3  Br  S   Cl  F                                  ##STR81## CH.sub.2 CCH.sub.2                                                                         CF.sub.3  Br  O   Cl  Cl                                 ##STR82## CH.sub.2 CCH.sub.2                                                                         CF.sub.3  Br  S   Cl  Cl                                 ##STR83##                                                                                 ##STR84##  CF.sub.3  H   O   Cl  Cl                                 ##STR85##                                                                                 ##STR86##  CF.sub.3  H   S   Cl  F                                  ##STR87##                                                                                 ##STR88##  CF.sub.3  H   S   Cl  Cl                                 ##STR89## CH.sub.2 Ph CF.sub.3  H   O   Cl  F                                  ##STR90## CH.sub.2 Ph CF.sub.3  H   O   Cl  Cl                                 ##STR91## CH.sub.2 Ph CF.sub.3  H   S   Cl  F                                  ##STR92## CH.sub.2 Ph CF.sub.3  H   S   Cl  Cl                                 ##STR93## H           CF.sub.3  H   O   Cl  Cl                                 ##STR94## H           CF.sub.3  H   S   Cl  F                                  ##STR95## H           CF.sub.3  H   S   Cl  Cl                                 ##STR96## H           CF.sub.3  H   O   Cl  F                                  ##STR97## iPr         CF.sub.3  H   O   Cl  Cl                                 ##STR98## iPr         CF.sub.3  H   S   Cl  F                                  ##STR99## iPr         CF.sub.3  H   S   Cl  Cl                                 ##STR100##                                                                               iPr         CF.sub.3  H   O   Cl  F                                 CH.sub.2 CHCH.sub.2                                                                        ##STR101## CF.sub.3  H   O   Cl  F                                 CH.sub.2 CHCH.sub.2                                                                        ##STR102## CF.sub.3  H   O   Cl  Cl                                CH.sub.2 CHCH.sub.2                                                                       CH.sub.2 Ph CF.sub.3  H   O   Cl  F                                 CH.sub.2 CHCH.sub.2                                                                       CH.sub.2 Ph CF.sub.3  H   O   Cl  Cl                                CH.sub.2 CHCH.sub.2                                                                       CH.sub.2 CHCH.sub.2                                                                        CF.sub.3  H   O   Cl  F                                 CH.sub.2 CHCH.sub.2                                                                       CH.sub.2 CHCH.sub.2                                                                        CF.sub.3  H   O   Cl  Cl                                CHF.sub.2  H           N(CH.sub.3).sub.2                                                                        H   O   Cl  F                                 CHF.sub.2  H           N(CH.sub.3).sub.2                                                                        H   S   Cl  F                                 CHF.sub.2  H           N(CH.sub.3).sub.2                                                                        H   O   Cl  Cl                                CHF.sub.2  H           N(CH.sub.3).sub.2                                                                        H   S   Cl  Cl                                CHF.sub.2  H           N(CH.sub.3).sub.2                                                                        Br  O   Cl  F                                 CHF.sub.2  H           N(CH.sub.3).sub.2                                                                        Br  S   Cl  F                                 CHF.sub.2  H           N(CH.sub.3).sub.2                                                                        Br  O   Cl  Cl                                CHF.sub.2  H           N(CH.sub.3).sub.2                                                                        Br  S   Cl  Cl                                CHF.sub.2  CH.sub.2 Ph N(CH.sub.3).sub.2                                                                        H   O   Cl  F                                 CHF.sub.2  CH.sub.2 Ph N(CH.sub.3).sub.2                                                                        H   S   Cl  F                                 CHF.sub.2  CH.sub.2 Ph N(CH.sub.3).sub.2                                                                        H   O   Cl  Cl                                CHF.sub.2  CH.sub.2 Ph N(CH.sub.3).sub.2                                                                        H   S   Cl  Cl                                CHF.sub.2  CH.sub.2 Ph N(CH.sub.3).sub.2                                                                        Br  O   Cl  F                                 CHF.sub.2  CH.sub.2 Ph N(CH.sub.3).sub.2                                                                        Br  S   Cl  F                                 CHF.sub.2  CH.sub.2 Ph N(CH.sub.3).sub.2                                                                        Br  O   Cl  Cl                                CHF.sub.2  CH.sub.2 Ph N(CH.sub.3).sub.2                                                                        Br  S   Cl  Cl                                CHF.sub.2                                                                                  ##STR103## N(CH.sub.3).sub.2                                                                        H   O   Cl  F                                 CHF.sub.2                                                                                  ##STR104## N(CH.sub.3).sub.2                                                                        H   S   Cl  F                                 CHF.sub.2                                                                                  ##STR105## N(CH.sub.3).sub.2                                                                        H   O   Cl  Cl                                CHF.sub.2                                                                                  ##STR106## N(CH.sub.3).sub.2                                                                        H   S   Cl  Cl                                CHF.sub.2                                                                                  ##STR107## N(CH.sub.3).sub.2                                                                        Br  O   Cl  F                                 CHF.sub.2                                                                                  ##STR108## N(CH.sub.3).sub.2                                                                        Br  S   Cl  F                                 CHF.sub.2                                                                                  ##STR109## N(CH.sub.3).sub.2                                                                        Br  O   Cl  Cl                                CHF.sub.2                                                                                  ##STR110## N(CH.sub.3).sub.2                                                                        Br  S   Cl  Cl                                CHF.sub.2  iPr         N(CH.sub.3).sub.2                                                                        H   O   Cl  F                                 CHF.sub.2  iPr         N(CH.sub.3).sub.2                                                                        H   S   Cl  F                                 CHF.sub.2  iPr         N(CH.sub.3).sub.2                                                                        H   O   Cl  Cl                                CHF.sub.2  iPr         N(CH.sub.3).sub.2                                                                        H   S   Cl  Cl                                CHF.sub.2  iPr         N(CH.sub.3).sub.2                                                                        Br  O   Cl  F                                 CHF.sub.2  iPr         N(CH.sub.3).sub.2                                                                        Br  S   Cl  F                                 CHF.sub.2  iPr         N(CH.sub.3).sub.2                                                                        Br  O   Cl  Cl                                CHF.sub.2  iPr         N(CH.sub.3).sub.2                                                                        Br  S   Cl  Cl                                CHF.sub.2  CH.sub.2 CCH.sub.2                                                                         N(CH.sub.3).sub.2                                                                        H   O   Cl  F                                 CHF.sub.2  CH.sub.2 CCH.sub.2                                                                         N(CH.sub.3).sub.2                                                                        H   S   Cl  F                                 CHF.sub.2  CH.sub.2 CCH.sub.2                                                                         N(CH.sub.3).sub.2                                                                        H   O   Cl  Cl                                CHF.sub.2  CH.sub.2 CCH.sub.2                                                                         N(CH.sub.3).sub.2                                                                        H   S   Cl  Cl                                CHF.sub.2  CH.sub.2 CCH.sub.2                                                                         N(CH.sub.3).sub.2                                                                        Br  O   Cl  F                                 CHF.sub.2  CH.sub.2 CCH.sub.2                                                                         N(CH.sub.3).sub.2                                                                        Br  S   Cl  F                                 CHF.sub.2  CH.sub.2 CCH.sub.2                                                                         N(CH.sub.3).sub.2                                                                        Br  O   Cl  Cl                                CHF.sub.2  CH.sub.2 CCH.sub.2                                                                         N(CH.sub.3).sub.2                                                                        Br  S   Cl  Cl                                CH.sub.3   H           N(CH.sub.3).sub.2                                                                        H   O   Cl  F                                 CH.sub.3   H           N(CH.sub.3).sub.2                                                                        H   S   Cl  F                                 CH.sub.3   H           N(CH.sub.3).sub.2                                                                        H   O   Cl  Cl                                CH.sub.3   H           N(CH.sub.3).sub.2                                                                        H   S   Cl  Cl                                CH.sub.3   H           N(CH.sub.3).sub.2                                                                        Br  O   Cl  F                                 CH.sub.3   H           N(CH.sub.3).sub.2                                                                        Br  S   Cl  F                                 CH.sub.3   H           N(CH.sub.3).sub.2                                                                        Br  O   Cl  Cl                                CH.sub.3   H           N(CH.sub.3).sub.2                                                                        Br  S   Cl  Cl                                CH.sub.3   CH.sub.2 Ph N(CH.sub.3).sub.2                                                                        H   O   Cl  F                                 CH.sub.3   CH.sub.2 Ph N(CH.sub.3).sub.2                                                                        H   S   Cl  F                                 CH.sub.3   CH.sub.2 Ph N(CH.sub.3).sub.2                                                                        H   O   Cl  Cl                                CH.sub.3   CH.sub.2 Ph N(CH.sub.3).sub.2                                                                        H   S   Cl  Cl                                CH.sub.3   CH.sub.2 Ph N(CH.sub.3).sub.2                                                                        Br  O   Cl  F                                 CH.sub.3   CH.sub.2 Ph N(CH.sub.3).sub.2                                                                        Br  S   Cl  F                                 CH.sub.3   CH.sub.2 Ph N(CH.sub.3).sub.2                                                                        Br  O   Cl  Cl                                CH.sub.3   CH.sub.2 Ph N(CH.sub.3).sub.2                                                                        Br  S   Cl  Cl                                CH.sub.3                                                                                   ##STR111## N CH.sub.3).sub.2                                                                        H   O   Cl  F                                 CH.sub.3                                                                                   ##STR112## N(CH.sub.3).sub.2                                                                        H   S   Cl  F                                 CH.sub.3                                                                                   ##STR113## N(CH.sub.3).sub.2                                                                        H   O   Cl  Cl                                CH.sub.3                                                                                   ##STR114## N(CH.sub.3).sub.2                                                                        H   S   Cl  Cl                                CH.sub.3                                                                                   ##STR115## N(CH.sub.3).sub.2                                                                        Br  O   Cl  F                                 CH.sub.3                                                                                   ##STR116## N(CH.sub.3).sub.2                                                                        Br  S   Cl  F                                 CH.sub.3                                                                                   ##STR117## N(CH.sub.3).sub.2                                                                        Br  O   Cl  Cl                                CH.sub.3                                                                                   ##STR118## N(CH.sub.3).sub.2                                                                        Br  S   Cl  Cl                                CH.sub.3   iPr         N(CH.sub.3).sub.2                                                                        H   O   Cl  F                                 CH.sub.3   iPr         N(CH.sub.3).sub.2                                                                        H   S   Cl  F                                 CH.sub.3   iPr         N(CH.sub.3).sub.2                                                                        H   O   Cl  Cl                                CH.sub.3   iPr         N(CH.sub.3).sub.2                                                                        H   S   Cl  Cl                                CH.sub.3   iPr         N(CH.sub.3).sub.2                                                                        Br  O   Cl  F                                 CH.sub.3   iPr         N(CH.sub.3).sub.2                                                                        Br  S   Cl  F                                 CH.sub.3   iPr         N(CH.sub.3).sub.2                                                                        Br  O   Cl  Cl                                CH.sub.3   iPr         N(CH.sub.3).sub.2                                                                        Br  S   Cl  Cl                                CH.sub.3   CH.sub.2 CCH.sub.2                                                                         N(CH.sub.3).sub.2                                                                        H   O   Cl  F                                 CH.sub.3   CH.sub.2 CCH.sub.2                                                                         N(CH.sub.3).sub.2                                                                        H   S   Cl  F                                 CH.sub.3   CH.sub.2 CCH.sub.2                                                                         N(CH.sub.3).sub.2                                                                        H   O   Cl  Cl                                CH.sub.3   CH.sub.2 CCH.sub.2                                                                         N(CH.sub.3).sub.2                                                                        H   S   Cl  Cl                                CH.sub.3   CH.sub.2 CCH.sub.2                                                                         N(CH.sub.3).sub.2                                                                        Br  O   Cl  F                                 CH.sub.3   CH.sub.2 CCH.sub.2                                                                         N(CH.sub.3).sub.2                                                                        Br  S   Cl  F                                 CH.sub.3   CH.sub.2 CCH.sub.2                                                                         N(CH.sub.3).sub.2                                                                        Br  O   Cl  Cl                                CH.sub.3   CH.sub.2 CCH.sub.2                                                                         N(CH.sub.3).sub.2                                                                        Br  S   Cl  Cl                                CH.sub.3   CH.sub.2 Ph (CH.sub.2).sub.3                                                                           O   Cl  F                                   CH.sub.3   CH.sub.2 Ph (CH.sub.2).sub.3                                                                           S   Cl  F                                   CH.sub.3   CH.sub.2 Ph (CH.sub.2).sub.3                                                                           O   Cl  Cl                                  CH.sub.3   CH.sub.2 Ph (CH.sub.2).sub.3                                                                           S   Cl  Cl                                  CH.sub.3                                                                                   ##STR119## (CH.sub.2).sub.3                                                                           O   Cl  F                                   CH.sub.3                                                                                   ##STR120## (CH.sub.2).sub.3                                                                           S   Cl  F                                   CH.sub.3                                                                                   ##STR121## (CH.sub.2).sub.3                                                                           O   Cl  Cl                                  CH.sub.3                                                                                   ##STR122## (CH.sub.2).sub.3                                                                           S   Cl  Cl                                  CH.sub.3   iPr         (CH.sub.2).sub.3                                                                           O   Cl  F                                   CH.sub.3   iPr         (CH.sub.2).sub.3                                                                           S   Cl  F                                   CH.sub.3   iPr         (CH.sub.2).sub.3                                                                           O   Cl  Cl                                  CH.sub.3   iPr         (CH.sub.2).sub.3                                                                           S   Cl  Cl                                  CH.sub.3   CH.sub.2 Ph (CH.sub.2).sub.4                                                                           O   Cl  F                                   CH.sub.3   CH.sub.2 Ph (CH.sub.2).sub.4                                                                           S   Cl  F                                   CH.sub.3   CH.sub.2 Ph (CH.sub.2).sub.4                                                                           O   Cl  Cl                                  CH.sub.3   CH.sub.2 Ph (CH.sub.2).sub.4                                                                           S   Cl  Cl                                  CH.sub.3                                                                                   ##STR123## (CH.sub.2).sub.4                                                                           O   Cl  F                                   CH.sub.3                                                                                   ##STR124## (CH.sub.2).sub.4                                                                           S   Cl  F                                   CH.sub.3                                                                                   ##STR125## (CH.sub.2).sub.4                                                                           O   Cl  Cl                                  CH.sub.3                                                                                   ##STR126## (CH.sub.2).sub.4                                                                           S   Cl  Cl                                  CH.sub.3   iPr         (CH.sub.2).sub.4                                                                           O   Cl  F                                   CH.sub.3   iPr         (CH.sub.2).sub.4                                                                           S   Cl  F                                   CH.sub.3   iPr         (CH.sub.2).sub.4                                                                           O   Cl  Cl                                  CH.sub.3   iPr         (CH.sub.2).sub.4                                                                           S   Cl  Cl                                  CN                                                                                         ##STR127## CF.sub.3  H   O   Cl  F                                 CN                                                                                         ##STR128## CF.sub.3  H   S   Cl  F                                 CN                                                                                         ##STR129## N(CH.sub.3).sub.2                                                                        H   O   Cl  Cl                                CN                                                                                         ##STR130## N(CH.sub.3).sub.2                                                                        Br  S   Cl  Cl                                COCH.sub.3                                                                                 ##STR131## CF.sub.3  H   O   Cl  F                                 COCH.sub.3                                                                                 ##STR132## CF.sub.3  H   S   Cl  F                                 COCH.sub.3                                                                                 ##STR133## N(CH.sub.3).sub.2                                                                        H   O   Cl  Cl                                COCH.sub.3                                                                                 ##STR134## N(CH.sub.3).sub.2                                                                        Br  S   Cl  Cl                                COCH.sub.3 iPr         N(CH.sub.3).sub.2                                                                        H   S   Cl  F                                 COCH.sub.3 iPr         N(CH.sub.3).sub.2                                                                        H   O   Cl  F                                 COCH.sub.3 iPr         N(CH.sub.3).sub.2                                                                        H   O   Cl  Cl                                COCH.sub.3 iPr         N(CH.sub.3).sub.2                                                                        Br  O   Cl  F                                 COCF.sub.3                                                                                 ##STR135## CF.sub.3  H   S   Cl  F                                 COCF.sub.3                                                                                 ##STR136## CF.sub.3  H   O   Cl  Cl                                COCF.sub.3                                                                                 ##STR137## CF.sub.3  H   O   Cl  F                                 COCF.sub.3 iPr         N(CH.sub.3).sub.2                                                                        H   S   Cl  F                                 COCF.sub.3 iPr         N(CH.sub.3).sub.2                                                                        H   O   Cl  Cl                                COCF.sub.3 iPr         N(CH.sub.3).sub.2                                                                        H   O   Cl  F                                 OCH.sub.3                                                                                  ##STR138## CF.sub.3  H   O   Cl  F                                 OCH.sub.3                                                                                  ##STR139## CF.sub.3  H   S   Cl  F                                 OCH.sub.3                                                                                  ##STR140## N(CH.sub.3).sub.2                                                                        H   O   Cl  Cl                                OCH.sub.3                                                                                  ##STR141## N(CH.sub.3).sub.2                                                                        Br  S   Cl  Cl                                CF.sub.2 H                                                                                 ##STR142## CF.sub.3  H   O   Cl  F                                 CF.sub.2 H                                                                                 ##STR143## CF.sub.3  H   S   Cl  F                                 CF.sub.2 H                                                                                 ##STR144## N(CH.sub.3).sub.2                                                                        H   O   Cl  Cl                                CF.sub.2 H                                                                                 ##STR145## N(CH.sub.3).sub.2                                                                        Br  S   Cl  Cl                                CF.sub.2 H iPr         N(CH.sub.3).sub.2                                                                        H   S   Cl  F                                 CF.sub.2 H iPr         N(CH.sub.3).sub.2                                                                        H   O   Cl  F                                 CF.sub.2 H iPr         N(CH.sub.3).sub.2                                                                        H   O   Cl  Cl                                CF.sub.2 H iPr         N(CH.sub.3).sub.2                                                                        Br  O   Cl  F                                 n-Bu                                                                                       ##STR146## CF.sub.3  H   S   Cl  F                                 n-Bu                                                                                       ##STR147## CF.sub.3  H   O   Cl  Cl                                n-Bu                                                                                       ##STR148## CF.sub.3  H   O   Cl  F                                 n-Bu       iPr         N(CH.sub.3).sub.2                                                                        H   S   Cl  F                                 n-Bu       iPr         N(CH.sub.3).sub.2                                                                        H   O   Cl  Cl                                n-Bu       iPr         N(CH.sub.3).sub.2                                                                        H   O   Cl  F                                  ##STR149##                                                                                ##STR150## CF.sub.3  H   S   Cl  F                                  ##STR151##                                                                                ##STR152## CF.sub.3  H   O   Cl  Cl                                 ##STR153##                                                                                ##STR154## CF.sub.3  H   O   Cl  F                                  ##STR155##                                                                                ##STR156## N(CH.sub.3).sub.2                                                                        H   S   Cl  F                                  ##STR157##                                                                                ##STR158## N(CH.sub.3).sub.2                                                                        H   O   Cl  Cl                                 ##STR159##                                                                                ##STR160## N(CH.sub.3).sub.2                                                                        H   O   Cl  F                                  ##STR161##                                                                               iPr         CF.sub.3  H   S   Cl  F                                  ##STR162##                                                                               iPr         CF.sub.3  H   O   Cl  Cl                                 ##STR163##                                                                               iPr         CF.sub.3  H   O   Cl  F                                  ##STR164##                                                                               iPr         N(CH.sub.3).sub.2                                                                        H   S   Cl  F                                  ##STR165##                                                                               iPr         N(CH.sub.3).sub.2                                                                        H   O   Cl  Cl                                 ##STR166##                                                                               iPr         N(CH.sub.3).sub.2                                                                        H   O   Cl  F                                 CH.sub.2 CMeCH.sub.2                                                                       ##STR167## N(CH.sub.3).sub.2                                                                        H   S   Cl  F                                 CH.sub.2 CMeCH.sub.2                                                                       ##STR168## N(CH.sub.3).sub.2                                                                        H   O   Cl  Cl                                CH.sub.2 CMeCH.sub.2                                                                       ##STR169## N(CH.sub.3).sub.2                                                                        H   S   Cl  F                                 CH.sub.2 CMeCH.sub.2                                                                       ##STR170## CF.sub.3  H   O   Cl  Cl                                CH.sub.2 CMeCH.sub.2                                                                       ##STR171## CF.sub.3  H   S   Cl  F                                 CH.sub.2 CMeCH.sub.2                                                                       ##STR172## CF.sub.3  H   O   Cl  Cl                                CH.sub.2 CMeCH.sub.2                                                                      iPr         N(CH.sub.3).sub.2                                                                        H   S   Cl  F                                 CH.sub.2 CMeCH.sub.2                                                                      iPr         N(CH.sub.3).sub.2                                                                        H   O   Cl  Cl                                CH.sub.2 CMeCH.sub.2                                                                      iPr         N(CH.sub.3).sub.2                                                                        H   S   Cl  F                                 CH.sub.2 CMeCH.sub.2                                                                      iPr         CF.sub.3  H   O   Cl  Cl                                CH.sub.2 CMeCH.sub.2                                                                      iPr         CF.sub.3  H   S   Cl  F                                 CH.sub.2 CMeCH.sub.2                                                                      iPr         CF.sub.3  H   O   Cl  Cl                                CH.sub.2 CMeCH.sub.2                                                                       ##STR173## N(CH.sub.3).sub.2                                                                        H   S   Cl  F                                 CH.sub.2 CMeCH.sub.2                                                                       ##STR174## N(CH.sub.3).sub.2                                                                        H   O   Cl  Cl                                CH.sub.2 CMeCH.sub.2                                                                       ##STR175## N(CH.sub.3).sub.2                                                                        H   S   Cl  F                                 CH.sub.2 CMeCH.sub.2                                                                       ##STR176## CF.sub.3  H   O   Cl  Cl                                CH.sub.2 CMeCH.sub.2                                                                       ##STR177## CF.sub.3  H   S   Cl  F                                 CH.sub.2 CMeCH.sub.2                                                                       ##STR178## CF.sub.3  H   O   Cl  Cl                                iPr        iPr         N(CH.sub.3).sub.2                                                                        H   S   Cl  F                                 iPr        iPr         N(CH.sub.3).sub.2                                                                        H   O   Cl  Cl                                iPr        iPr         N(CH.sub.3).sub.2                                                                        H   S   Cl  F                                 iPr        iPr         CF.sub.3  H   O   Cl  Cl                                iPr        iPr         CF.sub.3  H   S   Cl  F                                 iPr        iPr         CF.sub.3  H   O   Cl  Cl                                ______________________________________                                    

                  TABLE II                                                         ______________________________________                                          ##STR179##                                                                    R.sup.1   R.sup.3   R.sup.4                                                                              A   X   Y   R.sup.9                                  ______________________________________                                         CH.sub.3  CF.sub.3  H     O   Cl  F                                            CH.sub.3  CF.sub.3  H     S   Cl  F                                            CH.sub.3  CF.sub.3  H     O   Cl  Cl                                           CH.sub.3  CF.sub.3  H     S   Cl  Cl                                           CH.sub.3  N(CH.sub.3).sub.2                                                                        H     O   Cl  F                                            CH.sub.3  N(CH.sub.3).sub.2                                                                        H     S   Cl  F                                            CH.sub.3  N(CH.sub.3).sub.2                                                                        H     O   Cl  Cl                                           CH.sub.3  N(CH.sub.3).sub.2                                                                        H     S   Cl  Cl                                           CH.sub.3  CF.sub.3  Br    O   Cl  F                                            CH.sub.3  CF.sub.3  Br    S   Cl  F                                            CH.sub.3  CF.sub.3  Br    O   Cl  Cl                                           CH.sub.3  CF.sub.3  Br    S   Cl  Cl                                           CH.sub.3  N(CH.sub.3).sub.2                                                                        Br    O   Cl  F                                            CH.sub.3  N(CH.sub.3).sub.2                                                                        Br    S   Cl  F                                            CH.sub.3  N(CH.sub.3).sub.2                                                                        Br    O   Cl  Cl                                           CH.sub.3  N(CH.sub.3).sub.2                                                                        Br    S   Cl  Cl                                           CH.sub.3  (CH.sub.2).sub.3                                                                           O     Cl  F                                              CH.sub.3  (CH.sub.2).sub.3                                                                           O     Cl  Cl                                             CH.sub.3  (CH.sub.2).sub.3                                                                           S     Cl  F                                              CH.sub.3  (CH.sub.2).sub.3                                                                           S     Cl  Cl                                             CH.sub.3  (CH.sub.2).sub.4                                                                           O     Cl  F                                              CH.sub.3  (CH.sub.2).sub.4                                                                           O     Cl  F                                              CH.sub.3  (CH.sub.2).sub.4                                                                           S     Cl  F                                              CH.sub.3  (CH.sub.2).sub.4                                                                           S     Cl  F                                              CF.sub.3  CF.sub.3  H     O   Cl  F                                            CF.sub.3  CF.sub.3  H     S   Cl  F                                            CF.sub.3  CF.sub.3  H     O   Cl  Cl                                           CF.sub.3  CF.sub.3  H     S   Cl  Cl                                           CF.sub.3  N(CH.sub.3).sub.2                                                                        H     O   Cl  F                                            CF.sub.3  N(CH.sub.3).sub.2                                                                        H     S   Cl  F                                            CF.sub.3  N(CH.sub.3).sub.2                                                                        H     O   Cl  Cl                                           CF.sub.3  N(CH.sub.3).sub.2                                                                        H     S   Cl  Cl                                           CF.sub.3  CF.sub.3  Br    O   Cl  F                                            CF.sub.3  CF.sub.3  Br    S   Cl  F                                            CF.sub.3  CF.sub.3  Br    O   Cl  Cl                                           CF.sub.3  CF.sub.3  Br    S   Cl  Cl                                           CF.sub.3  N(CH.sub.3).sub.2                                                                        Br    O   Cl  F                                            CF.sub.3  N(CH.sub.3).sub.2                                                                        Br    S   Cl  F                                            CF.sub.3  N(CH.sub.3).sub.2                                                                        Br    O   Cl  Cl                                           CF.sub.3  N(CH.sub.3).sub.2                                                                        Br    S   Cl  Cl                                           CF.sub.3  (CH.sub.2).sub.3                                                                           O     Cl  F                                              CF.sub.3  (CH.sub.2).sub.3                                                                           O     Cl  Cl                                             CF.sub.3  (CH.sub.2).sub.3                                                                           S     Cl  F                                              CF.sub.3  (CH.sub.2).sub.3                                                                           S     Cl  Cl                                             CF.sub.3  (CH.sub.2).sub.4                                                                           O     Cl  F                                              CF.sub.3  (CH.sub.2).sub.4                                                                           O     Cl  F                                              CF.sub.3  (CH.sub.2).sub.4                                                                           S     Cl  F                                              CF.sub.3  (CH.sub.2).sub.4                                                                           S     Cl  F                                              CH.sub.2 CCH.sub.2                                                                       CF.sub.3  H     O   Cl  F                                            CH.sub.2 CCH.sub.2                                                                       CF.sub.3  H     S   Cl  F                                            CH.sub.2 CCH.sub.2                                                                       CF.sub.3  H     O   Cl  Cl                                           CH.sub.2 CCH.sub.2                                                                       CF.sub.3  H     O   Cl  F                                            CH.sub.2 CCH.sub.2                                                                       CHF.sub.2 H     O   Cl  F                                            CH.sub.2 CCH.sub.2                                                                       CHF.sub.2 H     O   Cl  Cl                                           CH.sub.2 CCH.sub.2                                                                       CHF.sub.2 H     S   Cl  F                                            CH.sub.2 CCH.sub.2                                                                       N(CH.sub.3).sub.2                                                                        H     O   Cl  F                                            CH.sub.2 CCH.sub.2                                                                       N(CH.sub.3).sub.2                                                                        H     S   Cl  F                                            CH.sub.2 CCH.sub.2                                                                       N(CH.sub.3).sub.2                                                                        H     O   Cl  Cl                                           CH.sub.2 CCH.sub.2                                                                       N(CH.sub.3).sub.2                                                                        H     S   Cl  Cl                                           CH.sub.2 CCH.sub.2                                                                       CF.sub.3  Br    O   Cl  F                                            CH.sub.2 CCH.sub.2                                                                       CF.sub.3  Br    S   Cl  F                                            CH.sub.2 CCH.sub.2                                                                       CF.sub.3  Br    O   Cl  Cl                                           CH.sub.2 CCH.sub.2                                                                       CF.sub.3  Br    S   Cl  Cl                                           CH.sub.2 CCH.sub.2                                                                       N(CH.sub.3).sub.2                                                                        Br    O   Cl  F                                            CH.sub.2 CCH.sub.2                                                                       N(CH.sub.3).sub.2                                                                        Br    S   Cl  F                                            CH.sub.2 CCH.sub.2                                                                       N(CH.sub.3).sub.2                                                                        Br    O   Cl  Cl                                           CH.sub.2 CCH.sub.2                                                                       N(CH.sub.3).sub.2                                                                        Br    S   Cl  Cl                                           CH.sub.2 CCH.sub.2                                                                       (CH.sub.2).sub.3                                                                           O     Cl  F                                              CH.sub.2 CCH.sub.2                                                                       (CH.sub.2).sub.3                                                                           O     Cl  Cl                                             CH.sub.2 CCH.sub.2                                                                       (CH.sub.2).sub.3                                                                           S     Cl  F                                              CH.sub.2 CCH.sub.2                                                                       (CH.sub.2).sub.3                                                                           S     Cl  Cl                                             CH.sub.2 CCH.sub.2                                                                       (CH.sub.2).sub.4                                                                           O     Cl  F                                              CH.sub.2 CCH.sub.2                                                                       (CH.sub.2).sub.4                                                                           O     Cl  F                                              CH.sub.2 CCH.sub.2                                                                       (CH.sub.2).sub.4                                                                           S     Cl  F                                              CH.sub.2 CCH.sub.2                                                                       (CH.sub.2).sub.4                                                                           S     Cl  F                                               ##STR180##                                                                              CF.sub.3  H     O   Cl  F                                             ##STR181##                                                                              CF.sub.3  H     S   Cl  F                                             ##STR182##                                                                              CF.sub.3  H     O   Cl  Cl                                            ##STR183##                                                                              CF.sub.3  H     O   Cl  F                                             ##STR184##                                                                              CHF.sub.2 H     O   Cl  F                                             ##STR185##                                                                              CHF.sub.2 H     O   Cl  Cl                                            ##STR186##                                                                              CHF.sub.2 H     S   Cl  F                                             ##STR187##                                                                              N(CH.sub.3).sub.2                                                                        H     O   Cl  F                                             ##STR188##                                                                              N(CH.sub.3).sub.2                                                                        H     S   Cl  F                                             ##STR189##                                                                              N(CH.sub.3).sub.2                                                                        H     O   Cl  Cl                                            ##STR190##                                                                              N(CH.sub.3).sub.2                                                                        H     S   Cl  Cl                                            ##STR191##                                                                              CF.sub.3  Br    O   Cl  F                                             ##STR192##                                                                              CF.sub.3  Br    S   Cl  F                                             ##STR193##                                                                              CF.sub.3  Br    O   Cl  Cl                                            ##STR194##                                                                              CF.sub.3  Br    S   Cl  Cl                                            ##STR195##                                                                              N(CH.sub.3).sub.2                                                                        Br    O   Cl  F                                             ##STR196##                                                                              N(CH.sub.3).sub.2                                                                        Br    S   Cl  F                                             ##STR197##                                                                              N(CH.sub.3).sub.2                                                                        Br    O   Cl  Cl                                            ##STR198##                                                                              N(CH.sub.3).sub.2                                                                        Br    S   Cl  Cl                                            ##STR199##                                                                              (CH.sub.2).sub.3                                                                           O     Cl  F                                               ##STR200##                                                                              (CH.sub.2).sub.3                                                                           O     Cl  Cl                                              ##STR201##                                                                              (CH.sub.2).sub.3                                                                           S     Cl  F                                               ##STR202##                                                                              (CH.sub.2).sub.3                                                                           S     Cl  Cl                                              ##STR203##                                                                              (CH.sub.2).sub.4                                                                           O     Cl  F                                               ##STR204##                                                                              (CH.sub.2).sub.4                                                                           O     Cl  F                                               ##STR205##                                                                              (CH.sub.2).sub.4                                                                           S     Cl  F                                               ##STR206##                                                                              (CH.sub.2).sub.4                                                                           S     Cl  F                                               ##STR207##                                                                              CF.sub.3  F     O   Cl  F                                             ##STR208##                                                                              CF.sub.3  F     O   Cl  Cl                                           n-Bu      CF.sub.3  H     O   Cl  F                                            n-Bu      CF.sub.3  H     S   Cl  F                                            COCH.sub.3                                                                               CF.sub.3  H     O   Cl  F                                            COCH.sub.3                                                                               CF.sub.3  H     O   Cl  Cl                                           CN        CF.sub.3  H     O   Cl  F                                            CN        CF.sub.3  H     O   Cl  Cl                                           CHF.sub.2 CF.sub.3  H     O   Cl  F                                            CHF.sub.2 CF.sub.3  H     O   Cl  Cl                                           CH.sub.3  CHF.sub.2 Br    O   Cl  F                                            CH.sub.3  CHF.sub.2 Br    S   Cl  F                                            CH.sub.3  CF.sub.3  F     O   Cl  F                                            CH.sub.3  CF.sub.3  F     S   Cl  F                                            CH.sub.3  CHF.sub.2 F     O   Cl  F                                            CH.sub.3  CHF.sub.2 F     S   Cl  F                                            CH.sub.3  CH.sub.2 F                                                                               F     O   Cl  F                                            CH.sub.3  CH.sub.2 F                                                                               F     S   Cl  F                                            CH.sub.3  CF.sub.3  Cl    O   Cl  F                                            CH.sub.3  CF.sub.3  Cl    S   Cl  F                                            CH.sub.3  CF.sub.3  Cl    O   Cl  F                                            CH.sub.3  CF.sub.3  Cl    S   Cl  F                                            CH.sub.3  CF.sub.3  H     O   Cl  F   CH.sub.2 CH.sub.3                        CH.sub.3  CF.sub.3  H     S   Cl  F   CH.sub.2 CH.sub.3                        CH.sub.3  CF.sub.3  H     O   Cl  Cl  CH.sub.2 CH.sub.3                        CH.sub.3  CF.sub.3  H     S   Cl  Cl  CH.sub.2 CH.sub.3                        CH.sub.3  CF.sub.3  H     O   Cl  F   CH.sub.2 CH.sub.2 CH.sub.3               CH.sub.3  CF.sub.3  H     S   Cl  F   CH.sub.2 CH.sub.2 CH.sub.3               CH.sub.3  CF.sub.3  H     O   Cl  Cl  CH.sub.2 CH.sub.2 CH.sub.3               CH.sub.3  CF.sub.3  H     S   Cl  Cl  CH.sub.2 CH.sub.2 CH.sub.3               CH.sub.3  CF.sub.3  H     O   Cl  F   CF.sub.3                                 CH.sub.3  CF.sub.3  H     S   Cl  F   CF.sub.3                                 CH.sub.3  CF.sub.3  H     O   Cl  Cl  CF.sub.3                                 CH.sub.3  CF.sub.3  H     S   Cl  Cl  CF.sub.3                                 CH.sub.3  CF.sub.3  H     O   Cl  F   CF.sub.2 H                               CH.sub.3  CF.sub.3  H     S   Cl  F   CF.sub.2 H                               CH.sub.3  CF.sub.3  H     O   Cl  Cl  CF.sub.2 H                               CH.sub.3  CF.sub.3  H     S   Cl  Cl  CF.sub.2 H                               CH.sub.3  CF.sub.3  H     O   Cl  F   CFH.sub.2                                CH.sub.3  CF.sub.3  H     S   Cl  F   CFH.sub.2                                CH.sub.3  CF.sub.3  H     O   Cl  Cl  CFH.sub.2                                CH.sub.3  CF.sub.3  H     S   Cl  Cl  CFH.sub.2                                CH.sub.3  CF.sub.3  H     O   Cl  F   CHCH.sub.2                               CH.sub.3  CF.sub.3  H     S   Cl  F   CHCH.sub.2                               CH.sub.3  CF.sub.3  H     O   Cl  Cl  CHCH.sub.2                               CH.sub.3  CF.sub.3  H     S   Cl  Cl  CHCH.sub.2                               CH.sub.3  CF.sub.3  H     O   Cl  F                                                                                   ##STR209##                              CH.sub.3  CF.sub.3  H     S   Cl  F                                                                                   ##STR210##                              CH.sub.3  CF.sub.3  H     O   Cl  Cl                                                                                  ##STR211##                              CH.sub.3  CF.sub.3  H     S   Cl  Cl                                                                                  ##STR212##                              CH.sub.3  CF.sub.3  H     O   Cl  F   CN                                       CH.sub.3  CF.sub.3  H     S   Cl  F   CN                                       CH.sub.3  CF.sub.3  H     O   Cl  Cl  CN                                       CH.sub.3  CF.sub.3  H     S   Cl  Cl  CN                                       CF.sub.3  CF.sub.3  H     O   Cl  F   CH.sub.2 CH.sub.3                        CF.sub.3  CF.sub.3  H     S   Cl  F   CH.sub.2 CH.sub.3                        CF.sub.3  CF.sub.3  H     O   Cl  Cl  CH.sub.2 CH.sub.3                        CF.sub.3  CF.sub.3  H     S   Cl  Cl  CH.sub.2 CH.sub.3                        CF.sub.3  CF.sub.3  H     O   Cl  F   CH.sub.2 CH.sub.2 CH.sub.3               CF.sub.3  CF.sub.3  H     S   Cl  F   CH.sub.2 CH.sub.2 CH.sub.3               CF.sub.3  CF.sub.3  H     O   Cl  Cl  CH.sub.2 CH.sub.2 CH.sub.3               CF.sub.3  CF.sub.3  H     S   Cl  Cl  CH.sub.2 CH.sub.2 CH.sub.3               CF.sub.3  CF.sub.3  H     O   Cl  F   CF.sub.3                                 CF.sub.3  CF.sub.3  H     S   Cl  F   CF.sub.3                                 CF.sub.3  CF.sub.3  H     O   Cl  Cl  CF.sub.3                                 CF.sub.3  CF.sub.3  H     S   Cl  Cl  CF.sub.3                                 CF.sub.3  CF.sub.3  H     O   Cl  F   CF.sub.2 H                               CF.sub.3  CF.sub.3  H     S   Cl  F   CF.sub.2 H                               CF.sub.3  CF.sub.3  H     O   Cl  Cl  CF.sub.2 H                               CF.sub.3  CF.sub.3  H     S   Cl  Cl  CF.sub.2 H                               CF.sub.3  CF.sub.3  H     O   Cl  F   CFH.sub.2                                CF.sub.3  CF.sub.3  H     S   Cl  F   CFH.sub.2                                CF.sub.3  CF.sub.3  H     O   Cl  Cl  CFH.sub.2                                CF.sub.3  CF.sub.3  H     S   Cl  Cl  CFH.sub.2                                CF.sub.3  CF.sub.3  H     O   Cl  F   CHCH.sub.2                               CF.sub.3  CF.sub.3  H     S   Cl  F   CHCH.sub.2                               CF.sub.3  CF.sub.3  H     O   Cl  Cl  CHCH.sub.2                               CF.sub.3  CF.sub.3  H     S   Cl  Cl  CHCH.sub.2                               CF.sub.3  CF.sub.3  H     O   Cl  F                                                                                   ##STR213##                              CF.sub.3  CF.sub.3  H     S   Cl  F                                                                                   ##STR214##                              CF.sub.3  CF.sub.3  H     O   Cl  Cl                                                                                  ##STR215##                              CF.sub.3  CF.sub.3  H     S   Cl  Cl                                                                                  ##STR216##                              CF.sub.3  CF.sub.3  H     O   Cl  F   CN                                       CF.sub.3  CF.sub.3  H     S   Cl  F   CN                                       CF.sub.3  CF.sub.3  H     O   Cl  Cl  CN                                       CF.sub.3  CF.sub.3  H     S   Cl  Cl  CN                                       CH.sub.3  CF.sub.3  Br    O   Cl  F   CH.sub.2 CH.sub.3                        CH.sub.3  CF.sub.3  Br    S   Cl  F   CH.sub.2 CH.sub.3                        CH.sub.3  CF.sub.3  Br    O   Cl  Cl  CH.sub.2 CH.sub.3                        CH.sub.3  CF.sub.3  Br    S   Cl  Cl  CH.sub.2 CH.sub.3                        CH.sub.3  CF.sub.3  Br    O   Cl  F   CH.sub.2 CH.sub.2 CH.sub.3               CH.sub.3  CF.sub.3  Br    S   Cl  F   CH.sub.2 CH.sub.2 CH.sub.3               CH.sub.3  CF.sub.3  Br    O   Cl  Cl  CH.sub.2 CH.sub.2 CH.sub.3               CH.sub.3  CF.sub.3  Br    S   Cl  Cl  CH.sub.2 CH.sub.2 CH.sub.3               CH.sub.3  CF.sub.3  Br    O   Cl  F   CF.sub.3                                 CH.sub.3  CF.sub.3  Br    S   Cl  F   CF.sub.3                                 CH.sub.3  CF.sub.3  Br    O   Cl  Cl  CF.sub.3                                 CH.sub.3  CF.sub.3  Br    S   Cl  Cl  CF.sub.3                                 CH.sub.3  CF.sub.3  Br    O   Cl  F   CF.sub.2 H                               CH.sub.3  CF.sub.3  Br    S   Cl  F   CF.sub.2 H                               CH.sub.3  CF.sub.3  Br    O   Cl  Cl  CF.sub.2 H                               CH.sub.3  CF.sub.3  Br    S   Cl  Cl  CF.sub.2 H                               CH.sub.3  CF.sub.3  Br    O   Cl  F   CFH.sub.2                                CH.sub.3  CF.sub.3  Br    S   Cl  F   CFH.sub.2                                CH.sub.3  CF.sub.3  Br    O   Cl  Cl  CFH.sub.2                                CH.sub.3  CF.sub.3  Br    S   Cl  Cl  CFH.sub.2                                CH.sub.3  CF.sub.3  Br    O   Cl  F   CHCH.sub.2                               CH.sub.3  CF.sub.3  Br    S   Cl  F   CHCH.sub.2                               CH.sub.3  CF.sub.3  Br    O   Cl  Cl  CHCH.sub.2                               CH.sub.3  CF.sub.3  Br    S   Cl  Cl  CHCH.sub.2                               CH.sub.3  CF.sub.3  Br    O   Cl  F                                                                                   ##STR217##                              CH.sub.3  CF.sub.3  Br    S   Cl  F                                                                                   ##STR218##                              CH.sub.3  CF.sub.3  Br    O   Cl  Cl                                                                                  ##STR219##                              CH.sub.3  CF.sub.3  Br    S   Cl  Cl                                                                                  ##STR220##                              CH.sub.3  CF.sub.3  Cl    O   Cl  F   CHCH.sub.2                               CH.sub.3  CF.sub.3  Cl    S   Cl  F   CHCH.sub.2                               CH.sub.3  CF.sub.3  Cl    O   Cl  Cl  CHCH.sub.2                               CH.sub.3  CF.sub.3  Cl    S   Cl  Cl  CHCH.sub.2                               CH.sub.3  CF.sub.3  Cl    O   Cl  F                                                                                   ##STR221##                              CH.sub.3  CF.sub.3  Cl    S   Cl  F                                                                                   ##STR222##                              CH.sub.3  CF.sub.3  Cl    O   Cl  Cl                                                                                  ##STR223##                              CH.sub.3  CF.sub.3  Cl    S   Cl  Cl                                                                                  ##STR224##                              CH.sub.3  CF.sub.3  Br    O   Cl  F   CN                                       CH.sub.3  CF.sub.3  Br    S   Cl  F   CN                                       CH.sub.3  CF.sub.3  Br    O   Cl  Cl  CN                                       CH.sub.3  CF.sub.3  Br    S   Cl  Cl  CN                                       CH.sub.3  (CH.sub.2).sub.3                                                                           O     Cl  F   CH.sub.2 CH.sub.3                          CH.sub.3  (CH.sub.2).sub.3                                                                           S     Cl  F   CH.sub.2 CH.sub.3                          CH.sub.3  (CH.sub.2).sub.3                                                                           O     Cl  Cl  CH.sub.2 CH.sub.3                          CH.sub.3  (CH.sub.2).sub.3                                                                           S     Cl  Cl  CH.sub.2 CH.sub.3                          CH.sub.3  (CH.sub.2).sub.4                                                                           O     Cl  F   CH.sub.2 CH.sub.3                          CH.sub.3  (CH.sub.2).sub.4                                                                           S     Cl  F   CH.sub.2 CH.sub.3                          CH.sub.3  (CH.sub.2).sub.4                                                                           O     Cl  Cl  CH.sub.2 CH.sub.3                          CH.sub.3  (CH.sub.2).sub.4                                                                           S     Cl  Cl  CH.sub.2 CH.sub.3                          CH.sub.3  (CH.sub.2).sub.3                                                                           O     Cl  F   CF.sub.3                                   CH.sub.3  (CH.sub.2).sub.3                                                                           S     Cl  F   CF.sub.3                                   CH.sub.3  (CH.sub.2).sub.3                                                                           O     Cl  Cl  CF.sub.3                                   CH.sub.3  (CH.sub.2).sub.3                                                                           S     Cl  Cl  CF.sub.3                                   CH.sub.3  (CH.sub.2).sub.4                                                                           S     Cl  F   CF.sub.3                                   CH.sub.3  (CH.sub.2).sub.4                                                                           O     Cl  F   CF.sub.3                                   CH.sub.3  (CH.sub.2).sub.4                                                                           S     Cl  Cl  CF.sub.3                                   CH.sub.3  (CH.sub.2).sub.4                                                                           O     Cl  Cl  CF.sub.3                                   CH.sub.3  (CH.sub.2).sub.3                                                                           O     Cl  F   CF.sub.2 H                                 CH.sub.3  (CH.sub.2).sub.3                                                                           S     Cl  F   CF.sub.2 H                                 CH.sub.3  (CH.sub.2).sub.3                                                                           O     Cl  Cl  CF.sub.2 H                                 CH.sub.3  (CH.sub.2).sub.3                                                                           S     Cl  Cl  CF.sub.2 H                                 CH.sub.3  (CH.sub.2).sub.4                                                                           O     Cl  F   CF.sub.2 H                                 CH.sub.3  (CH.sub.2).sub.4                                                                           S     Cl  F   CF.sub.2 H                                 CH.sub.3  (CH.sub.2).sub.4                                                                           O     Cl  Cl  CF.sub.2 H                                 CH.sub.3  (CH.sub.2).sub.4                                                                           S     Cl  Cl  CF.sub.2 H                                 CH.sub.3  (CH.sub.2).sub.3                                                                           O     Cl  F   CFH.sub.2                                  CH.sub.3  (CH.sub.2).sub.3                                                                           S     Cl  F   CFH.sub.2                                  CH.sub.3  (CH.sub.2).sub.3                                                                           O     Cl  Cl  CFH.sub.2                                  CH.sub.3  (CH.sub.2).sub.3                                                                           S     Cl  Cl  CFH.sub.2                                  CH.sub.3  (CH.sub.2).sub.4                                                                           O     Cl  F   CFH.sub.2                                  CH.sub.3  (CH.sub.2).sub.4                                                                           S     Cl  F   CFH.sub.2                                  CH.sub.3  (CH.sub.2).sub.4                                                                           O     Cl  Cl  CFH.sub.2                                  CH.sub.3  (CH.sub.2).sub.4                                                                           S     Cl  Cl  CFH.sub.2                                  CH.sub.3  (CH.sub.2).sub.3                                                                           O     Cl  F   CHCH.sub.2                                 CH.sub.3  (CH.sub.2).sub.3                                                                           S     Cl  F   CHCH.sub.2                                 CH.sub.3  (CH.sub.2).sub.3                                                                           O     Cl  Cl  CHCH.sub.2                                 CH.sub.3  (CH.sub.2).sub.3                                                                           S     Cl  Cl  CHCH.sub.2                                 CH.sub.3  (CH.sub.2).sub.4                                                                           O     Cl  F   CHCH.sub.2                                 CH.sub.3  (CH.sub.2).sub.4                                                                           S     Cl  F   CHCH.sub.2                                 CH.sub.3  (CH.sub.2).sub.4                                                                           O     Cl  Cl  CHCH.sub.2                                 CH.sub.3  (CH.sub.2).sub.4                                                                           S     Cl  Cl  CHCH.sub.2                                 CH.sub.3  (CH.sub.2).sub.3                                                                           O     Cl  F                                                                                   ##STR225##                                CH.sub.3  (CH.sub.2).sub.3                                                                           S     Cl  F                                                                                   ##STR226##                                CH.sub.3  (CH.sub.2).sub.3                                                                           O     Cl  Cl                                                                                  ##STR227##                                CH.sub.3  (CH.sub.2).sub.3                                                                           S     Cl  Cl                                                                                  ##STR228##                                CH.sub.3  (CH.sub.2).sub.4                                                                           O     Cl  F                                                                                   ##STR229##                                CH.sub.3  (CH.sub.2).sub.4                                                                           S     Cl  F                                                                                   ##STR230##                                CH.sub.3  (CH.sub.2).sub.4                                                                           O     Cl  Cl                                                                                  ##STR231##                                CH.sub.3  (CH.sub.2).sub.4                                                                           S     Cl  Cl                                                                                  ##STR232##                                CH.sub.3  (CH.sub.2).sub.3                                                                           O     Cl  F   CN                                         CH.sub.3  (CH.sub.2).sub.3                                                                           S     Cl  F   CN                                         CH.sub.3  (CH.sub.2).sub.3                                                                           O     Cl  Cl  CN                                         CH.sub.3  (CH.sub.2).sub.3                                                                           S     Cl  Cl  CN                                         CH.sub.3  (CH.sub.2).sub.4                                                                           O     Cl  F   CN                                         CH.sub.3  (CH.sub.2).sub.4                                                                           S     Cl  F   CN                                         CH.sub.3  (CH.sub.2).sub.4                                                                           O     Cl  Cl  CN                                         CH.sub.3  (CH.sub.2).sub.4                                                                           S     Cl  Cl  CN                                         CH.sub.3  CF.sub.3  H     O   Cl  F   CH.sub.2 OH                              CH.sub.3  CF.sub.3  H     O   Cl  F   CH.sub.2 OC(O)CH.sub.3                   CH.sub.3  CF.sub.3  H     O   Cl  F   CO.sub.2 CH.sub.3                        CH.sub.3  CF.sub.3  H     O   Cl  F   CON(CH.sub.3).sub.2                      CH.sub.3  N(CH.sub.3).sub.2                                                                        H     O   Cl  F   CH.sub.2 OH                              CH.sub.3  N(CH.sub.3).sub.2                                                                        H     O   Cl  F   CH.sub.2 OC(O)CH.sub.3                   CH.sub.3  N(CH.sub.3).sub.2                                                                        H     O   Cl  F   CO.sub.2 CH.sub.3                        CH.sub.3  CF.sub.3  Br    O   Cl  F   CH.sub.2 OH                              CH.sub.3  CF.sub.3  Br    O   Cl  F   CH.sub.2 OC(O)CH.sub.3                   CH.sub.3  CF.sub.3  Br    O   Cl  F   CO.sub.2 CH.sub.3                        CH.sub.3  CF.sub.3  Br    S   Cl  F   CH.sub.2 OH                              ______________________________________                                    

                  TABLE III                                                        ______________________________________                                          ##STR233##                                                                    R.sup.1   R.sup.3  A     X   Y   R.sup.2    Z                                  ______________________________________                                         CH.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  F   H          H                                  CH.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  Cl  H          H                                  CH.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  F   H          H                                  CH.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  Cl  H          H                                  CH.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  F                                                                                   ##STR234##                                                                               H                                  CH.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  Cl                                                                                  ##STR235##                                                                               H                                  CH.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  F                                                                                   ##STR236##                                                                               H                                  CH.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  Cl                                                                                  ##STR237##                                                                               H                                  CH.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  F   CH.sub.2 Ph                                                                               H                                  CH.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  Cl  CH.sub.2 Ph                                                                               H                                  CH.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  F   CH.sub.2 Ph                                                                               H                                  CH.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  Cl  CH.sub.2 Ph                                                                               H                                  CH.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  F   iPr        H                                  CH.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  Cl  iPr        H                                  CH.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  F   iPr        H                                  CH.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  Cl  iPr        H                                  CH.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  F                                                                                   ##STR238##                                                                               H                                  CH.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  Cl                                                                                  ##STR239##                                                                               H                                  CH.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  F                                                                                   ##STR240##                                                                               H                                  CH.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  Cl                                                                                  ##STR241##                                                                               H                                  CH.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  F   CH.sub.2 CHCH.sub.2                                                                       H                                  CH.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  Cl  CH.sub.2 CHCH.sub.2                                                                       H                                  CH.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  F   CH.sub.2 CHCH.sub.2                                                                       H                                  CH.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  Cl  CH.sub.2 CHCH.sub.2                                                                       H                                  CH.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  F   CHMeCO.sub.2 Me                                                                           H                                  CH.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  Cl  CHMeCO.sub.2 Me                                                                           H                                  CH.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  F   CHMeCO.sub.2 Me                                                                           H                                  CH.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  Cl  CHMeCO.sub.2 Me                                                                           H                                  CH.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  F   CH(CH.sub.3)CH.sub.2                          CH.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  Cl  CH(CH.sub.3)CH.sub.2                          CH.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  F   CH(CH.sub.3)CH.sub.2                          CH.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  Cl  CH(CH.sub.3)CH.sub.2                          CH.sub.3  CF.sub.3 O     Cl  F   H          H                                  CH.sub.3  CF.sub.3 O     Cl  Cl  H          H                                  CH.sub.3  CF.sub.3 S     Cl  F   H          H                                  CH.sub.3  CF.sub.3 S     Cl  Cl  H          H                                  CH.sub.3  CF.sub.3 O     Cl  F                                                                                   ##STR242##                                                                               H                                  CH.sub.3  CF.sub.3 O     Cl  Cl                                                                                  ##STR243##                                                                               H                                  CH.sub.3  CF.sub.3 S     Cl  F                                                                                   ##STR244##                                                                               H                                  CH.sub.3  CF.sub.3 S     Cl  Cl                                                                                  ##STR245##                                                                               H                                  CH.sub.3  CF.sub.3 O     Cl  F   CH.sub.2 Ph                                                                               H                                  CH.sub.3  CF.sub.3 O     Cl  Cl  CH.sub.2 Ph                                                                               H                                  CH.sub.3  CF.sub.3 S     Cl  F   CH.sub.2 Ph                                                                               H                                  CH.sub.3  CF.sub.3 S     Cl  Cl  CH.sub.2 Ph                                                                               H                                  CH.sub.3  CF.sub.3 O     Cl  F   iPr        H                                  CH.sub.3  CF.sub.3 O     Cl  Cl  iPr        H                                  CH.sub.3  CF.sub.3 S     Cl  F   iPr        H                                  CH.sub.3  CF.sub.3 S     Cl  Cl  iPr        H                                  CH.sub.3  CF.sub.3 O     Cl  F                                                                                   ##STR246##                                                                               H                                  CH.sub.3  CF.sub.3 O     Cl  Cl                                                                                  ##STR247##                                                                               H                                  CH.sub.3  CF.sub.3 S     Cl  F                                                                                   ##STR248##                                                                               H                                  CH.sub.3  CF.sub.3 S     Cl  Cl                                                                                  ##STR249##                                                                               H                                  CH.sub.3  CF.sub.3 O     Cl  F   CH.sub.2 CHCH.sub.2                                                                       H                                  CH.sub.3  CF.sub.3 O     Cl  Cl  CH.sub.2 CHCH.sub.2                                                                       H                                  CH.sub.3  CF.sub.3 S     Cl  F   CH.sub.2 CHCH.sub.2                                                                       H                                  CH.sub.3  CF.sub.3 S     Cl  Cl  CH.sub.2 CHCH.sub.2                                                                       H                                  CH.sub.3  CF.sub.3 O     Cl  F   CHMeCO.sub.2 Me                                                                           H                                  CH.sub.3  CF.sub.3 O     Cl  Cl  CHMeCO.sub.2 Me                                                                           H                                  CH.sub.3  CF.sub.3 S     Cl  F   CHMeCO.sub.2 Me                                                                           H                                  CH.sub.3  CF.sub.3 S     Cl  Cl  CHMeCO.sub.2 Me                                                                           H                                  CH.sub.3  CF.sub.3 O     Cl  F   CH(CH.sub.3)CH.sub.2                          CH.sub.3  CF.sub.3 O     Cl  Cl  CH(CH.sub.3)CH.sub.2                          CH.sub.3  CF.sub.3 S     Cl  F   CH(CH.sub.3)CH.sub.2                          CH.sub.3  CF.sub.3 S     Cl  Cl  CH(CH.sub.3)CH.sub.2                          CF.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  F   H          H                                  CF.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  Cl  H          H                                  CF.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  F   H          H                                  CF.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  Cl  H          H                                  CF.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  F                                                                                   ##STR250##                                                                               H                                  CF.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  Cl                                                                                  ##STR251##                                                                               H                                  CF.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  F                                                                                   ##STR252##                                                                               H                                  CF.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  Cl                                                                                  ##STR253##                                                                               H                                  CF.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  F   CH.sub.2 Ph                                                                               H                                  CF.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  Cl  CH.sub.2 Ph                                                                               H                                  CF.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  F   CH.sub.2 Ph                                                                               H                                  CF.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  Cl  CH.sub.2 Ph                                                                               H                                  CF.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  F   iPr        H                                  CF.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  Cl  iPr        H                                  CF.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  F   iPr        H                                  CF.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  Cl  iPr        H                                  CF.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  F                                                                                   ##STR254##                                                                               H                                  CF.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  Cl                                                                                  ##STR255##                                                                               H                                  CF.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  F                                                                                   ##STR256##                                                                               H                                  CF.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  Cl                                                                                  ##STR257##                                                                               H                                  CF.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  F   CH.sub.2 CHCH.sub.2                                                                       H                                  CF.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  Cl  CH.sub.2 CHCH.sub.2                                                                       H                                  CF.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  F   CH.sub.2 CHCH.sub.2                                                                       H                                  CF.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  Cl  CH.sub.2 CHCH.sub.2                                                                       H                                  CF.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  F   CHMeCO.sub.2 Me                                                                           H                                  CF.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  Cl  CHMeCO.sub.2 Me                                                                           H                                  CF.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  F   CHMeCO.sub.2 Me                                                                           H                                  CF.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  Cl  CHMeCO.sub.2 Me                                                                           H                                  CF.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  F   CH(CH.sub.3)CH.sub.2                          CF.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  Cl  CH(CH.sub.3)CH.sub.2                          CF.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  F   CH(CH.sub.3)CH.sub.2                          CF.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  Cl  CH(CH.sub.3)CH.sub.2                          CF.sub.3  CF.sub.3 O     Cl  F   H          H                                  CF.sub.3  CF.sub.3 O     Cl  Cl  H          H                                  CF.sub.3  CF.sub.3 S     Cl  F   H          H                                  CF.sub.3  CF.sub.3 S     Cl  Cl  H          H                                  CF.sub.3  CF.sub.3 O     Cl  F                                                                                   ##STR258##                                                                               H                                  CF.sub.3  CF.sub.3 O     Cl  Cl                                                                                  ##STR259##                                                                               H                                  CF.sub.3  CF.sub.3 S     Cl  F                                                                                   ##STR260##                                                                               H                                  CF.sub.3  CF.sub.3 S     Cl  Cl                                                                                  ##STR261##                                                                               H                                  CF.sub.3  CF.sub.3 O     Cl  F   CH.sub.2 Ph                                                                               H                                  CF.sub.3  CF.sub.3 O     Cl  Cl  CH.sub.2 Ph                                                                               H                                  CF.sub.3  CF.sub.3 S     Cl  F   CH.sub.2 Ph                                                                               H                                  CF.sub.3  CF.sub.3 S     Cl  Cl  CH.sub.2 Ph                                                                               H                                  CF.sub.3  CF.sub.3 O     Cl  F   Pr         H                                  CF.sub.3  CF.sub.3 O     Cl  Cl  Pr         H                                  CF.sub.3  CF.sub.3 S     Cl  F   Pr         H                                  CF.sub.3  CF.sub.3 S     Cl  Cl  Pr         H                                  CF.sub.3  CF.sub.3 O     Cl  F                                                                                   ##STR262##                                                                               H                                  CF.sub.3  CF.sub.3 O     Cl  Cl                                                                                  ##STR263##                                                                               H                                  CF.sub.3  CF.sub.3 S     Cl  F                                                                                   ##STR264##                                                                               H                                  CF.sub.3  CF.sub.3 S     Cl  Cl                                                                                  ##STR265##                                                                               H                                  CF.sub.3  CF.sub.3 O     Cl  F   CH.sub.2 CHCH.sub.2                                                                       H                                  CF.sub.3  CF.sub.3 O     Cl  Cl  CH.sub.2 CHCH.sub.2                                                                       H                                  CF.sub.3  CF.sub.3 S     Cl  F   CH.sub.2 CHCH.sub.2                                                                       H                                  CF.sub.3  CF.sub.3 S     Cl  Cl  CH.sub.2 CHCH.sub.2                                                                       H                                  CF.sub.3  CF.sub.3 O     Cl  F   CHMeCO.sub.2 Me                                                                           H                                  CF.sub.3  CF.sub.3 O     Cl  Cl  CHMeCO.sub.2 Me                                                                           H                                  CF.sub.3  CF.sub.3 S     Cl  F   CHMeCO.sub.2 Me                                                                           H                                  CF.sub.3  CF.sub.3 S     Cl  Cl  CHMeCO.sub.2 Me                                                                           H                                  CF.sub.3  CF.sub.3 O     Cl  F   CH(CH.sub.3)CH.sub.2                          CF.sub.3  CF.sub.3 O     Cl  Cl  CH(CH.sub.3)CH.sub.2                          CF.sub.3  CF.sub.3 S     Cl  F   CH(CH.sub.3)CH.sub.2                          CF.sub.3  CF.sub.3 S     Cl  Cl  CH(CH.sub.3)CH.sub.2                          i-Pr      N(CH.sub.3).sub.2                                                                       O     Cl  F   H          H                                  i-Pr      N(CH.sub.3).sub.2                                                                       O     Cl  Cl  H          H                                  i-Pr      N(CH.sub.3).sub.2                                                                       S     Cl  F   H          H                                  i-Pr      N(CH.sub.3).sub.2                                                                       S     Cl  Cl  H          H                                  i-Pr      N(CH.sub.3).sub.2                                                                       O     Cl  F                                                                                   ##STR266##                                                                               H                                  i-Pr      N(CH.sub.3).sub.2                                                                       O     Cl  Cl                                                                                  ##STR267##                                                                               H                                  i-Pr      N(CH.sub.3).sub.2                                                                       S     Cl  F                                                                                   ##STR268##                                                                               H                                  i-Pr      N(CH.sub.3).sub.2                                                                       S     Cl  Cl                                                                                  ##STR269##                                                                               H                                  i-Pr      N(CH.sub.3).sub.2                                                                       O     Cl  F   CH.sub.2 Ph                                                                               H                                  i-Pr      N(CH.sub.3).sub.2                                                                       O     Cl  Cl  CH.sub.2 Ph                                                                               H                                  i-Pr      N(CH.sub.3).sub.2                                                                       S     Cl  F   CH.sub.2 Ph                                                                               H                                  i-Pr      N(CH.sub.3).sub.2                                                                       S     Cl  Cl  CH.sub.2 Ph                                                                               H                                  i-Pr      N(CH.sub.3).sub.2                                                                       O     Cl  F   iPr        H                                  i-Pr      N(CH.sub.3).sub.2                                                                       O     Cl  Cl  iPr        H                                  i-Pr      N(CH.sub.3).sub.2                                                                       S     Cl  F   iPr        H                                  i-Pr      N(CH.sub.3).sub.2                                                                       S     Cl  Cl  iPr        H                                  i-Pr      N(CH.sub.3).sub.2                                                                       O     Cl  F                                                                                   ##STR270##                                                                               H                                  i-Pr      N(CH.sub.3).sub.2                                                                       O     Cl  Cl                                                                                  ##STR271##                                                                               H                                  i-Pr      N(CH.sub.3).sub.2                                                                       S     Cl  F                                                                                   ##STR272##                                                                               H                                  i-Pr      N(CH.sub.3).sub.2                                                                       S     Cl  Cl                                                                                  ##STR273##                                                                               H                                  i-Pr      N(CH.sub.3).sub.2                                                                       O     Cl  F   CH.sub.2 CHCH.sub.2                                                                       H                                  i-Pr      N(CH.sub.3).sub.2                                                                       O     Cl  Cl  CH.sub.2 CHCH.sub.2                                                                       H                                  i-Pr      N(CH.sub.3).sub.2                                                                       S     Cl  F   CH.sub.2 CHCH.sub.2                                                                       H                                  i-Pr      N(CH.sub.3).sub.2                                                                       S     Cl  Cl  CH.sub.2 CHCH.sub.2                                                                       H                                  i-Pr      N(CH.sub.3).sub.2                                                                       O     Cl  F   CHMeCO.sub.2 Me                                                                           H                                  i-Pr      N(CH.sub.3).sub.2                                                                       O     Cl  Cl  CHMeCO.sub.2 Me                                                                           H                                  i-Pr      N(CH.sub.3).sub.2                                                                       S     Cl  F   CHMeCO.sub.2 Me                                                                           H                                  i-Pr      N(CH.sub.3).sub.2                                                                       S     Cl  Cl  CHMeCO.sub.2 Me                                                                           H                                  i-Pr      N(CH.sub.3).sub.2                                                                       O     Cl  F   CH(CH.sub.3)CH.sub.2                          i-Pr      N(CH.sub.3).sub.2                                                                       O     Cl  Cl  CH(CH.sub.3)CH.sub.2                          i-Pr      N(CH.sub.3).sub.2                                                                       S     Cl  F   CH(CH.sub.3)CH.sub.2                          i-Pr      N(CH.sub.3).sub.2                                                                       S     Cl  Cl  CH(CH.sub.3)CH.sub.2                          i-Pr      CF.sub.3 O     Cl  F   H          H                                  i-Pr      CF.sub.3 O     Cl  Cl  H          H                                  i-Pr      CF.sub.3 S     Cl  F   H          H                                  i-Pr      CF.sub.3 S     Cl  Cl  H          H                                  i-Pr      CF.sub.3 O     Cl  F                                                                                   ##STR274##                                                                               H                                  i-Pr      CF.sub.3 O     Cl  Cl                                                                                  ##STR275##                                                                               H                                  i-Pr      CF.sub.3 S     Cl  F                                                                                   ##STR276##                                                                               H                                  i-Pr      CF.sub.3 S     Cl  Cl                                                                                  ##STR277##                                                                               H                                  i-Pr      CF.sub.3 O     Cl  F   CH.sub.2 Ph                                                                               H                                  i-Pr      CF.sub.3 O     Cl  Cl  CH.sub.2 Ph                                                                               H                                  i-Pr      CF.sub.3 S     Cl  F   CH.sub.2 Ph                                                                               H                                  i-Pr      CF.sub.3 S     Cl  Cl  CH.sub.2 Ph                                                                               H                                  i-Pr      CF.sub.3 O     Cl  F   iPr        H                                  i-Pr      CF.sub.3 O     Cl  Cl  iPr        H                                  i-Pr      CF.sub.3 S     Cl  F   iPr        H                                  i-Pr      CF.sub.3 S     Cl  Cl  iPr        H                                  i-Pr      CF.sub.3 O     Cl  F                                                                                   ##STR278##                                                                               H                                  i-Pr      CF.sub.3 O     Cl  Cl                                                                                  ##STR279##                                                                               H                                  i-Pr      CF.sub.3 S     Cl  F                                                                                   ##STR280##                                                                               H                                  i-Pr      CF.sub.3 S     Cl  Cl                                                                                  ##STR281##                                                                               H                                  i-Pr      CF.sub.3 O     Cl  F   CH.sub.2 CHCH.sub.2                                                                       H                                  i-Pr      CF.sub.3 O     Cl  Cl  CH.sub.2 CHCH.sub.2                                                                       H                                  i-Pr      CF.sub.3 S     Cl  F   CH.sub.2 CHCH.sub.2                                                                       H                                  i-Pr      CF.sub.3 S     Cl  Cl  CH.sub.2 CHCH.sub.2                                                                       H                                  i-Pr      CF.sub.3 O     Cl  F   CHMeCO.sub.2 Me                                                                           H                                  i-Pr      CF.sub.3 O     Cl  Cl  CHMeCO.sub.2 Me                                                                           H                                  i-Pr      CF.sub.3 S     Cl  F   CHMeCO.sub.2 Me                                                                           H                                  i-Pr      CF.sub.3 S     Cl  Cl  CHMeCO.sub.2 Me                                                                           H                                  i-Pr      CF.sub.3 O     Cl  F   CH(CH.sub.3)CH.sub.2                          i-Pr      CF.sub.3 O     Cl  Cl  CH(CH.sub.3)CH.sub.2                          i-Pr      CF.sub.3 S     Cl  F   CH(CH.sub.3)CH.sub.2                          i-Pr      CF.sub.3 S     Cl  Cl  CH(CH.sub.3)CH.sub.2                           ##STR282##                                                                              N(CH.sub.3).sub.2                                                                       O     Cl  F   H          H                                   ##STR283##                                                                              N(CH.sub.3).sub.2                                                                       O     Cl  Cl  H          H                                   ##STR284##                                                                              N(CH.sub.3).sub.2                                                                       S     Cl  F   H          H                                   ##STR285##                                                                              N(CH.sub.3).sub.2                                                                       S     Cl  Cl  H          H                                   ##STR286##                                                                              N(CH.sub.3).sub.2                                                                       O     Cl  F                                                                                   ##STR287##                                                                               H                                   ##STR288##                                                                              N(CH.sub.3).sub.2                                                                       O     Cl  Cl                                                                                  ##STR289##                                                                               H                                   ##STR290##                                                                              N(CH.sub.3).sub.2                                                                       S     Cl  F                                                                                   ##STR291##                                                                               H                                   ##STR292##                                                                              N(CH.sub.3).sub.2                                                                       S     Cl  Cl                                                                                  ##STR293##                                                                               H                                   ##STR294##                                                                              N(CH.sub.3).sub.2                                                                       O     Cl  F   CH.sub.2 Ph                                                                               H                                   ##STR295##                                                                              N(CH.sub.3).sub.2                                                                       O     Cl  Cl  CH.sub.2 Ph                                                                               H                                   ##STR296##                                                                              N(CH.sub.3).sub.2                                                                       S     Cl  F   CH.sub.2 Ph                                                                               H                                   ##STR297##                                                                              N(CH.sub.3).sub.2                                                                       S     Cl  Cl  CH.sub.2 Ph                                                                               H                                   ##STR298##                                                                              N(CH.sub.3).sub.2                                                                       O     Cl  F   iPr        H                                   ##STR299##                                                                              N(CH.sub.3).sub.2                                                                       O     Cl  Cl  iPr        H                                   ##STR300##                                                                              N(CH.sub.3).sub.2                                                                       S     Cl  F   iPr        H                                   ##STR301##                                                                              N(CH.sub.3).sub.2                                                                       S     Cl  Cl  iPr        H                                   ##STR302##                                                                              N(CH.sub.3).sub.2                                                                       O     Cl  F                                                                                   ##STR303##                                                                               H                                   ##STR304##                                                                              N(CH.sub.3).sub.2                                                                       O     Cl  Cl                                                                                  ##STR305##                                                                               H                                   ##STR306##                                                                              N(CH.sub.3).sub.2                                                                       S     Cl  F                                                                                   ##STR307##                                                                               H                                   ##STR308##                                                                              N(CH.sub.3).sub.2                                                                       S     Cl  Cl                                                                                  ##STR309##                                                                               H                                   ##STR310##                                                                              N(CH.sub.3).sub.2                                                                       O     Cl  F   CH.sub.2 CHCH.sub.2                                                                       H                                   ##STR311##                                                                              N(CH.sub.3).sub.2                                                                       O     Cl  Cl  CH.sub.2 CHCH.sub.2                                                                       H                                   ##STR312##                                                                              N(CH.sub.3).sub.2                                                                       S     Cl  F   CH.sub.2 CHCH.sub.2                                                                       H                                   ##STR313##                                                                              N(CH.sub.3).sub.2                                                                       S     Cl  Cl  CH.sub.2 CHCH.sub.2                                                                       H                                   ##STR314##                                                                              N(CH.sub.3).sub.2                                                                       O     Cl  F   CHMeCO.sub.2 Me                                                                           H                                   ##STR315##                                                                              N(CH.sub.3).sub.2                                                                       O     Cl  Cl  CHMeCO.sub.2 Me                                                                           H                                   ##STR316##                                                                              N(CH.sub.3).sub.2                                                                       S     Cl  F   CHMeCO.sub.2 Me                                                                           H                                   ##STR317##                                                                              N(CH.sub.3).sub.2                                                                       S     Cl  Cl  CHMeCO.sub.2 Me                                                                           H                                   ##STR318##                                                                              N(CH.sub.3).sub.2                                                                       O     Cl  F   CH(CH.sub.3)CH.sub.2                           ##STR319##                                                                              N(CH.sub.3).sub.2                                                                       O     Cl  Cl  CH(CH.sub.3)CH.sub.2                           ##STR320##                                                                              N(CH.sub.3).sub.2                                                                       S     Cl  F   CH(CH.sub.3)CH.sub.2                           ##STR321##                                                                              N(CH.sub.3).sub.2                                                                       S     Cl  Cl  CH(CH.sub.3)CH.sub.2                           ##STR322##                                                                              CF.sub.3 O     Cl  F   H          H                                   ##STR323##                                                                              CF.sub.3 O     Cl  Cl  H          H                                   ##STR324##                                                                              CF.sub.3 S     Cl  F   H          H                                   ##STR325##                                                                              CF.sub.3 S     Cl  Cl  H          H                                   ##STR326##                                                                              CF.sub.3 O     Cl  F                                                                                   ##STR327##                                                                               H                                   ##STR328##                                                                              CF.sub.3 O     Cl  Cl                                                                                  ##STR329##                                                                               H                                   ##STR330##                                                                              CF.sub.3 S     Cl  F                                                                                   ##STR331##                                                                               H                                   ##STR332##                                                                              CF.sub.3 S     Cl  Cl                                                                                  ##STR333##                                                                               H                                   ##STR334##                                                                              CF.sub.3 O     Cl  F   CH.sub.2 Ph                                                                               H                                   ##STR335##                                                                              CF.sub.3 O     Cl  Cl  CH.sub.2 Ph                                                                               H                                   ##STR336##                                                                              CF.sub.3 S     Cl  F   CH.sub.2 Ph                                                                               H                                   ##STR337##                                                                              CF.sub.3 S     Cl  Cl  CH.sub.2 Ph                                                                               H                                   ##STR338##                                                                              CF.sub.3 O     Cl  F   iPr        H                                   ##STR339##                                                                              CF.sub.3 O     Cl  Cl  iPr        H                                   ##STR340##                                                                              CF.sub.3 S     Cl  F   iPr        H                                   ##STR341##                                                                              CF.sub.3 S     Cl  Cl  iPr        H                                   ##STR342##                                                                              CF.sub.3 O     Cl  F                                                                                   ##STR343##                                                                               H                                   ##STR344##                                                                              CF.sub.3 O     Cl  Cl                                                                                  ##STR345##                                                                               H                                   ##STR346##                                                                              CF.sub.3 S     Cl  F                                                                                   ##STR347##                                                                               H                                   ##STR348##                                                                              CF.sub.3 S     Cl  Cl                                                                                  ##STR349##                                                                               H                                   ##STR350##                                                                              CF.sub.3 O     Cl  F   CH.sub.2 CHCH.sub.2                                                                       H                                   ##STR351##                                                                              CF.sub.3 O     Cl  Cl  CH.sub.2 CHCH.sub.2                                                                       H                                   ##STR352##                                                                              CF.sub.3 S     Cl  F   CH.sub.2 CHCH.sub.2                                                                       H                                   ##STR353##                                                                              CF.sub.3 S     Cl  Cl  CH.sub.2 CHCH.sub.2                                                                       H                                   ##STR354##                                                                              CF.sub.3 O     Cl  F   CHMeCO.sub.2 Me                                                                           H                                   ##STR355##                                                                              CF.sub.3 O     Cl  Cl  CHMeCO.sub.2 Me                                                                           H                                   ##STR356##                                                                              CF.sub.3 S     Cl  F   CHMeCO.sub.2 Me                                                                           H                                   ##STR357##                                                                              CF.sub.3 S     Cl  Cl  CHMeCO.sub.2 Me                                                                           H                                   ##STR358##                                                                              CF.sub.3 O     Cl  F   CH(CH.sub.3)CH.sub.2                           ##STR359##                                                                              CF.sub.3 O     Cl  Cl  CH(CH.sub.3)CH.sub.2                           ##STR360##                                                                              CF.sub.3 S     Cl  F   CH(CH.sub.3)CH.sub.2                           ##STR361##                                                                              CF.sub.3 S     Cl  Cl  CH(CH.sub.3)CH.sub.2                          CHO       CF.sub.3 O     Cl  F                                                                                   ##STR362##                                                                               H                                  CHO       CF.sub.3 O     Cl  Cl                                                                                  ##STR363##                                                                               H                                  CHO       CF.sub.3 O     Cl  F   CH(CH.sub.3)CH.sub.2                          CHO       CF.sub.3 O     Cl  Cl  CH(CH.sub.3)CH.sub.2                          COCH.sub.3                                                                               CF.sub.3 O     Cl  F                                                                                   ##STR364##                                                                               H                                  COCH.sub.3                                                                               CF.sub.3 O     Cl  Cl                                                                                  ##STR365##                                                                               H                                  COCH.sub.3                                                                               CF.sub.3 O     Cl  F   CH(CH.sub.3)CH.sub.2                          COCH.sub.3                                                                               CF.sub.3 O     Cl  Cl  CH(CH.sub.3)CH.sub.2                          COCH.sub.3                                                                               N(CH.sub.3).sub.2                                                                       O     Cl  F                                                                                   ##STR366##                                                                               H                                  COCH.sub.3                                                                               N(CH.sub.3).sub.2                                                                       O     Cl  Cl                                                                                  ##STR367##                                                                               H                                  COCH.sub.3                                                                               N(CH.sub.3).sub.2                                                                       O     Cl  F   CH(CH.sub.3)CH.sub.2                          COCH.sub.3                                                                               N(CH.sub.3).sub.2                                                                       O     Cl  Cl  CH(CH.sub.3)CH.sub.2                          CHF.sub.2 CF.sub.3 O     Cl  F                                                                                   ##STR368##                                                                               H                                  CHF.sub.2 CF.sub.3 O     Cl  Cl                                                                                  ##STR369##                                                                               H                                  CHF.sub.2 CF.sub.3 O     Cl  F   CH(CH.sub.3)CH.sub.2                          CHF.sub.2 CF.sub.3 O     Cl  Cl  CH(CH.sub.3)CH.sub.2                          CHF.sub.2 N(CH.sub.3).sub.2                                                                       O     Cl  F                                                                                   ##STR370##                                                                               H                                  CHF.sub.2 N(CH.sub.3).sub.2                                                                       O     Cl  Cl                                                                                  ##STR371##                                                                               H                                  CHF.sub.2 N(CH.sub.3).sub.2                                                                       O     Cl  F   CH(CH.sub.3)CH.sub.2                          CHF.sub.2 N(CH.sub.3).sub.2                                                                       O     Cl  Cl  CH(CH.sub.3)CH.sub.2                          CH.sub.2 F                                                                               CF.sub.3 O     Cl  F                                                                                   ##STR372##                                                                               H                                  CH.sub.2 F                                                                               CF.sub.3 O     Cl  Cl                                                                                  ##STR373##                                                                               H                                  CH.sub.2 F                                                                               CF.sub.3 O     Cl  F   CH(CH.sub.3)CH.sub.2                          CH.sub.2 F                                                                               CF.sub.3 O     Cl  Cl  CH(CH.sub.3)CH.sub.2                          CH.sub.2 F                                                                               N(CH.sub.3).sub.2                                                                       O     Cl  F                                                                                   ##STR374##                                                                               H                                  CH.sub.2 F                                                                               N(CH.sub.3).sub.2                                                                       O     Cl  Cl                                                                                  ##STR375##                                                                               H                                  CH.sub.2 F                                                                               N(CH.sub.3).sub.2                                                                       O     Cl  F   CH(CH.sub.3)CH.sub.2                          CH.sub.2 F                                                                               N(CH.sub.3).sub.2                                                                       O     Cl  Cl  CH(CH.sub.3)CH.sub.2                           ##STR376##                                                                              N(CH.sub.3).sub.2                                                                       O     Cl  F                                                                                   ##STR377##                                                                               H                                   ##STR378##                                                                              N(CH.sub.3).sub.2                                                                       O     Cl  Cl                                                                                  ##STR379##                                                                               H                                   ##STR380##                                                                              N(CH.sub.3).sub.2                                                                       O     Cl  F   CH(CH.sub.3)CH.sub.2                           ##STR381##                                                                              N(CH.sub.3).sub.2                                                                       O     Cl  Cl  CH(CH.sub.3)CH.sub.2                          CH.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  F   CH(CF.sub.3)CH.sub.2                          CH.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  Cl  CH(CF.sub.3)CH.sub.2                          CH.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  F   CH(CF.sub.3)CH.sub.2                          CH.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  Cl  CH(CF.sub.3)CH.sub.2                          CH.sub.3  CF.sub.3 O     Cl  F   CH(CF.sub.3)CH.sub.2                          CH.sub.3  CF.sub.3 O     Cl  Cl  CH(CF.sub.3)CH.sub.2                          CH.sub.3  CF.sub.3 S     Cl  F   CH(CF.sub.3)CH.sub.2                          CH.sub.3  CF.sub.3 S     Cl  Cl  CH(CF.sub.3)CH.sub.2                          CF.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  F   CH(CF.sub.3)CH.sub.2                          CF.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  Cl  CH(CF.sub.3)CH.sub.2                          CF.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  F   CH(CF.sub.3)CH.sub.2                          CF.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  Cl  CH(CF.sub.3)CH.sub.2                          CF.sub.3  CF.sub.3 O     Cl  F   CH(CF.sub.3)CH.sub.2                          CF.sub.3  CF.sub.3 O     Cl  Cl  CH(CF.sub.3)CH.sub.2                          CF.sub.3  CF.sub.3 S     Cl  F   CH(CF.sub.3)CH.sub.2                          CF.sub.3  CF.sub.3 S     Cl  Cl  CH(CF.sub.3)CH.sub.2                          CH.sub.2 F                                                                               N(CH.sub.3).sub.2                                                                       O     Cl  F   CH(CF.sub.3)CH.sub.2                          CH.sub.2 F                                                                               N(CH.sub.3).sub.2                                                                       O     Cl  Cl  CH(CF.sub.3)CH.sub.2                          CH.sub.2 F                                                                               N(CH.sub.3).sub.2                                                                       S     Cl  F   CH(CF.sub.3)CH.sub.2                          CH.sub.2 F                                                                               N(CH.sub.3).sub.2                                                                       S     Cl  Cl  CH(CF.sub.3)CH.sub.2                          CH.sub.2 F                                                                               CF.sub.3 O     Cl  F   CH(CF.sub.3)CH.sub.2                          CH.sub.2 F                                                                               CF.sub.3 O     Cl  Cl  CH(CF.sub.3)CH.sub.2                          CH.sub.2 F                                                                               CF.sub.3 S     Cl  F   CH(CF.sub.3)CH.sub.2                          CH.sub.2 F                                                                               CF.sub.3 S     Cl  Cl  CH(CF.sub.3)CH.sub.2                          CH.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  F   CH(CHCH.sub.2)CH.sub.2                        CH.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  Cl  CH(CHCH.sub.2)CH.sub.2                        CH.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  F   CH(CHCH.sub.2)CH.sub.2                        CH.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  Cl  CH(CHCH.sub.2)CH.sub.2                        CH.sub.3  CF.sub.3 O     Cl  F   CH(CHCH.sub.2)CH.sub.2                        CH.sub.3  CF.sub.3 O     Cl  Cl  CH(CHCH.sub.2)CH.sub.2                        CH.sub.3  CF.sub.3 S     Cl  F   CH(CHCH.sub.2)CH.sub.2                        CH.sub.3  CF.sub.3 S     Cl  Cl  CH(CHCH.sub.2)CH.sub.2                        CF.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  F   CH(CHCH.sub.2)CH.sub.2                        CF.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  Cl  CH(CHCH.sub.2)CH.sub.2                        CF.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  F   CH(CHCH.sub.2)CH.sub.2                        CF.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  Cl  CH(CHCH.sub.2)CH.sub.2                        CF.sub.3  CF.sub.3 O     Cl  F   CH(CHCH.sub.2)CH.sub.2                        CF.sub.3  CF.sub.3 O     Cl  Cl  CH(CHCH.sub.2)CH.sub.2                        CF.sub.3  CF.sub.3 S     Cl  F   CH(CHCH.sub.2)CH.sub.2                        CF.sub.3  CF.sub.3 S     Cl  Cl  CH(CHCH.sub.2)CH.sub.2                        CH.sub.2 F                                                                               N(CH.sub.3).sub.2                                                                       O     Cl  F   CH(CHCH.sub.2)CH.sub.2                        CH.sub.2 F                                                                               N(CH.sub.3).sub.2                                                                       O     Cl  Cl  CH(CHCH.sub.2)CH.sub.2                        CH.sub.2 F                                                                               N(CH.sub.3).sub.2                                                                       S     Cl  F   CH(CHCH.sub.2)CH.sub.2                        CH.sub.2 F                                                                               N(CH.sub.3).sub.2                                                                       S     Cl  Cl  CH(CHCH.sub.2)CH.sub.2                        CH.sub.2 F                                                                               CF.sub.3 O     Cl  F   CH(CHCH.sub.2)CH.sub.2                        CH.sub.2 F                                                                               CF.sub.3 O     Cl  Cl  CH(CHCH.sub.2)CH.sub.2                        CH.sub.2 F                                                                               CF.sub.3 S     Cl  F   CH(CHCH.sub.2)CH.sub.2                        CH.sub.2 F                                                                               CF.sub.3 S     Cl  Cl  CH(CHCH.sub.2)CH.sub.2                        CH.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  F                                                                                   ##STR382##                                   CH.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  Cl                                                                                  ##STR383##                                   CH.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  F                                                                                   ##STR384##                                   CH.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  Cl                                                                                  ##STR385##                                   CH.sub.3  CF.sub.3 O     Cl  F                                                                                   ##STR386##                                   CH.sub.3  CF.sub.3 O     Cl  Cl                                                                                  ##STR387##                                   CH.sub.3  CF.sub.3 S     Cl  F                                                                                   ##STR388##                                   CH.sub.3  CF.sub.3 S     Cl  Cl                                                                                  ##STR389##                                   CF.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  F                                                                                   ##STR390##                                   CF.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  Cl                                                                                  ##STR391##                                   CF.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  F                                                                                   ##STR392##                                   CF.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  Cl                                                                                  ##STR393##                                   CF.sub.3  CF.sub.3 O     Cl  F                                                                                   ##STR394##                                   CF.sub.3  CF.sub.3 O     Cl  Cl                                                                                  ##STR395##                                   CF.sub.3  CF.sub.3 S     Cl  F                                                                                   ##STR396##                                   CF.sub.3  CF.sub.3 S     Cl  Cl                                                                                  ##STR397##                                   CH.sub.2 F                                                                               N(CH.sub.3).sub.2                                                                       O     Cl  F                                                                                   ##STR398##                                   CH.sub.2 F                                                                               N(CH.sub.3).sub.2                                                                       O     Cl  Cl                                                                                  ##STR399##                                   CH.sub.2 F                                                                               N(CH.sub.3).sub.2                                                                       S     Cl  F                                                                                   ##STR400##                                   CH.sub.2 F                                                                               N(CH.sub.3).sub.2                                                                       S     Cl  Cl                                                                                  ##STR401##                                   CH.sub.2 F                                                                               CF.sub.3 O     Cl  F                                                                                   ##STR402##                                   CH.sub.2 F                                                                               CF.sub.3 O     Cl  Cl                                                                                  ##STR403##                                   CH.sub.2 F                                                                               CF.sub.3 S     Cl  F                                                                                   ##STR404##                                   CH.sub.2 F                                                                               CF.sub.3 S     Cl  Cl                                                                                  ##STR405##                                   CH.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  F   CH(CH.sub.2 CH.sub.3)CH.sub.2                 CH.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  Cl  CH(CH.sub.2 CH.sub.3)CH.sub.2                 CH.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  F   CH(CH.sub.2 CH.sub.3)CH.sub.2                 CH.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  Cl  CH(CH.sub.2 CH.sub.3)CH.sub.2                 CH.sub.3  CF.sub.3 O     Cl  F   CH(CH.sub.2 CH.sub.3)CH.sub.2                 CH.sub.3  CF.sub.3 O     Cl  Cl  CH(CH.sub.2 CH.sub.3)CH.sub.2                 CH.sub.3  CF.sub.3 S     Cl  F   CH(CH.sub.2 CH.sub.3)CH.sub.2                 CH.sub.3  CF.sub.3 S     Cl  Cl  CH(CH.sub.2 CH.sub.3)CH.sub.2                 CF.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  F   CH(CH.sub.2 CH.sub.3)CH.sub.2                 CF.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  Cl  CH(CH.sub.2 CH.sub.3)CH.sub.2                 CF.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  F   CH(CH.sub.2 CH.sub.3)CH.sub.2                 CF.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  Cl  CH(CH.sub.2 CH.sub.3)CH.sub.2                 CF.sub.3  CF.sub.3 O     Cl  F   CH(CH.sub.2 CH.sub.3)CH.sub.2                 CF.sub.3  CF.sub.3 O     Cl  Cl  CH(CH.sub.2 CH.sub.3)CH.sub.2                 CF.sub.3  CF.sub.3 S     Cl  F   CH(CH.sub.2 CH.sub.3)CH.sub.2                 CF.sub.3  CF.sub.3 S     Cl  Cl  CH(CH.sub.2 CH.sub.3)CH.sub.2                 CH.sub.2 F                                                                               N(CH.sub.3).sub.2                                                                       O     Cl  F   CH(CH.sub.2 CH.sub.3)CH.sub.2                 CH.sub.2 F                                                                               N(CH.sub.3).sub.2                                                                       O     Cl  Cl  CH(CH.sub.2 CH.sub.3)CH.sub.2                 CH.sub.2 F                                                                               N(CH.sub.3).sub.2                                                                       S     Cl  F   CH(CH.sub.2 CH.sub.3)CH.sub.2                 CH.sub.2 F                                                                               N(CH.sub.3).sub.2                                                                       S     Cl  Cl  CH(CH.sub.2 CH.sub.3)CH.sub.2                 CH.sub.2 F                                                                               CF.sub.3 O     Cl  F   CH(CH.sub.2 CH.sub.3)CH.sub.2                 CH.sub.2 F                                                                               CF.sub.3 O     Cl  Cl  CH(CH.sub.2 CH.sub.3)CH.sub.2                 CH.sub.2 F                                                                               CF.sub.3 S     Cl  F   CH(CH.sub.2 CH.sub.3)CH.sub.2                 CH.sub.2 F                                                                               CF.sub.3 S     Cl  Cl  CH(CH.sub.2 CH.sub.3)CH.sub.2                 CH.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  F   CH(CH.sub.2 F)CH.sub.2                        CH.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  Cl  CH(CH.sub.2 F)CH.sub.2                        CH.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  F   CH(CH.sub.2 F)CH.sub.2                        CH.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  Cl  CH(CH.sub.2 F)CH.sub.2                        CH.sub.3  CF.sub.3 O     Cl  F   CH(CH.sub.2 F)CH.sub.2                        CH.sub.3  CF.sub.3 O     Cl  Cl  CH(CH.sub.2 F)CH.sub.2                        CH.sub.3  CF.sub.3 S     Cl  F   CH(CH.sub.2 F)CH.sub.2                        CH.sub.3  CF.sub.3 S     Cl  Cl  CH(CH.sub.2 F)CH.sub.2                        CF.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  F   CH(CH.sub.2 F)CH.sub.2                        CF.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  Cl  CH(CH.sub.2 F)CH.sub.2                        CF.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  F   CH(CH.sub.2 F)CH.sub.2                        CF.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  Cl  CH(CH.sub.2 F)CH.sub.2                        CF.sub.3  CF.sub.3 O     Cl  F   CH(CH.sub.2 F)CH.sub.2                        CF.sub.3  CF.sub.3 O     Cl  Cl  CH(CH.sub.2 F)CH.sub.2                        CF.sub.3  CF.sub.3 S     Cl  F   CH(CH.sub.2 F)CH.sub.2                        CF.sub.3  CF.sub.3 S     Cl  Cl  CH(CH.sub.2 F)CH.sub.2                        CH.sub.2 F                                                                               N(CH.sub.3).sub.2                                                                       O     Cl  F   CH(CH.sub.2 F)CH.sub.2                        CH.sub.2 F                                                                               N(CH.sub.3).sub.2                                                                       O     Cl  Cl  CH(CH.sub.2 F)CH.sub.2                        CH.sub.2 F                                                                               N(CH.sub.3).sub.2                                                                       S     Cl  F   CH(CH.sub.2 F)CH.sub.2                        CH.sub.2 F                                                                               N(CH.sub.3).sub.2                                                                       S     Cl  Cl  CH(CH.sub.2 F)CH.sub.2                        CH.sub.2 F                                                                               CF.sub.3 O     Cl  F   CH(CH.sub.2 F)CH.sub.2                        CH.sub.2 F                                                                               CF.sub.3 O     Cl  Cl  CH(CH.sub.2 F)CH.sub.2                        CH.sub.2 F                                                                               CF.sub.3 S     Cl  F   CH(CH.sub.2 F)CH.sub.2                        CH.sub.2 F                                                                               CF.sub.3 S     Cl  Cl  CH(CH.sub.2 F)CH.sub.2                        CH.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  F   CH(CN)CH.sub.2                                CH.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  Cl  CH(CN)CH.sub.2                                CH.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  F   CH(CN)CH.sub.2                                CH.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  Cl  CH(CN)CH.sub.2                                CH.sub.3  CF.sub.3 O     Cl  F   CH(CN)CH.sub.2                                CH.sub.3  CF.sub.3 O     Cl  Cl  CH(CN)CH.sub.2                                CH.sub.3  CF.sub.3 S     Cl  F   CH(CN)CH.sub.2                                CH.sub.3  CF.sub.3 S     Cl  Cl  CH(CN)CH.sub.2                                CF.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  F   CH(CN)CH.sub.2                                CF.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  Cl  CH(CN)CH.sub.2                                CF.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  F   CH(CN)CH.sub.2                                CF.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  Cl  CH(CN)CH.sub.2                                CF.sub.3  CF.sub.3 O     Cl  F   CH(CN)CH.sub.2                                CF.sub.3  CF.sub.3 O     Cl  Cl  CH(CN)CH.sub.2                                CF.sub.3  CF.sub.3 S     Cl  F   CH(CN)CH.sub.2                                CF.sub.3  CF.sub.3 S     Cl  Cl  CH(CN)CH.sub.2                                CH.sub.2 F                                                                               N(CH.sub.3).sub.2                                                                       O     Cl  F   CH(CN)CH.sub.2                                CH.sub.2 F                                                                               N(CH.sub.3).sub.2                                                                       O     Cl  Cl  CH(CN)CH.sub.2                                CH.sub.2 F                                                                               N(CH.sub.3).sub.2                                                                       S     Cl  F   CH(CN)CH.sub.2                                CH.sub.2 F                                                                               N(CH.sub.3).sub.2                                                                       S     Cl  Cl  CH(CN)CH.sub.2                                CH.sub.2 F                                                                               CF.sub.3 O     Cl  F   CH(CN)CH.sub.2                                CH.sub.2 F                                                                               CF.sub.3 O     Cl  Cl  CH(CN)CH.sub.2                                CH.sub.2 F                                                                               CF.sub.3 S     Cl  F   CH(CN)CH.sub.2                                CH.sub.2 F                                                                               CF.sub.3 S     Cl  Cl  CH(CN)CH.sub.2                                CH.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  F   CH(CF.sub.2 H)CH.sub.2                        CH.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  Cl  CH(CF.sub.2 H)CH.sub.2                        CH.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  F   CH(CF.sub.2 H)CH.sub.2                        CH.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  Cl  CH(CF.sub.2 H)CH.sub.2                        CH.sub.3  CF.sub.3 O     Cl  F   CH(CF.sub.2 H)CH.sub.2                        CH.sub.3  CF.sub.3 O     Cl  Cl  CH(CF.sub.2 H)CH.sub.2                        CH.sub.3  CF.sub.3 S     Cl  F   CH(CF.sub.2 H)CH.sub.2                        CH.sub.3  CF.sub.3 S     Cl  Cl  CH(CF.sub.2 H)CH.sub.2                        CF.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  F   CH(CF.sub.2 H)CH.sub.2                        CF.sub.3  N(CH.sub.3).sub.2                                                                       O     Cl  Cl  CH(CF.sub.2 H)CH.sub.2                        CF.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  F   CH(CF.sub.2 H)CH.sub.2                        CF.sub.3  N(CH.sub.3).sub.2                                                                       S     Cl  Cl  CH(CF.sub.2 H)CH.sub.2                        CF.sub.3  CF.sub.3 O     Cl  F   CH(CF.sub.2 H)CH.sub.2                        CF.sub.3  CF.sub.3 O     Cl  Cl  CH(CF.sub.2 H)CH.sub.2                        CF.sub.3  CF.sub.3 S     Cl  F   CH(CF.sub.2 H)CH.sub.2                        CF.sub.3  CF.sub.3 S     Cl  Cl  CH(CF.sub.2 H)CH.sub.2                        CH.sub.2 F                                                                               N(CH.sub.3).sub.2                                                                       O     Cl  F   CH(CF.sub.2 H)CH.sub.2                        CH.sub.2 F                                                                               N(CH.sub.3).sub.2                                                                       O     Cl  Cl  CH(CF.sub.2 H)CH.sub.2                        CH.sub.2 F                                                                               N(CH.sub.3).sub.2                                                                       S     Cl  F   CH(CF.sub.2 H)CH.sub.2                        CH.sub.2 F                                                                               N(CH.sub.3).sub.2                                                                       S     Cl  Cl  CH(CF.sub.2 H)CH.sub.2                        CH.sub.2 F                                                                               CF.sub.3 O     Cl  F   CH(CF.sub.2 H)CH.sub.2                        CH.sub.2 F                                                                               CF.sub.3 O     Cl  Cl  CH(CF.sub.2 H)CH.sub.2                        CH.sub.2 F                                                                               CF.sub.3 S     Cl  F   CH(CF.sub.2 H)CH.sub.2                        CH.sub.2 F                                                                               CF.sub.3 S     Cl  Cl  CH(CF.sub.2 H)CH.sub.2                        ______________________________________                                    

FORMULATION

Compounds of this invention will generally be used in formulation with an agriculturally suitable carrier comprising a liquid or solid diluent or an organic solvent. Use formulations include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates, dry flowables and the like, consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature. Sprayable formulations can be extended in suitable media and used at spray volumes from about one to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up 100 weight percent.

    ______________________________________                                                     Weight Percent                                                                 Active                                                                         Ingredient                                                                              Diluent   Surfactant                                      ______________________________________                                         Wettable Powders                                                                             25-90       0-74     1-10                                        Oil Suspensions,                                                                              5-50      40-95     0-15                                        Emulsions, Solutions,                                                          (including Emulsifiable                                                        Concentrates)                                                                  Dusts          1-25      70-99     0-5                                         Granules and Pellets                                                                         0.01-99       5-99.99                                                                               0-15                                        High Strength 90-99       0-10     0-2                                         Compositions                                                                   ______________________________________                                    

Typical solid diluents are described in Watkins, et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, N.J. Typical liquid diluents and solvents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950. McCutcheon's Detergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, N.J., as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth, etc.

Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer mill or fluid energy mill. Water-dispersible granules can be produced be agglomerating a fine powder composition; see for example, Cross et al., Pesticide Formulations, Washington, D.C., 1988, pp 251-259. Suspensions are prepared by wet-milling; see, for example, U.S. Pat. No. 3,060,084. Granules and pellets can be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, pp 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and following, and WO 91/13546. Pellets can be prepared as described in U.S. Pat. No. 4,172,714. Water-dispersible and water-soluble granules can also be prepared as taught in DE 3,246,493.

For further information regarding the art of formulation, see U.S. Pat. No. 3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples 10-41; U.S. Pat. No. 3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; U.S. Pat. No. 2,891,855, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pp 81-96; and Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989.

In the following Examples, all percentages are by weight and all formulations are worked up in conventional ways. Compound numbers refer to compounds in Table IV.

    ______________________________________                                         Example A                                                                      High Strength Concentrate                                                      Compound 1              98.5%                                                  silica aerogel          0.5%                                                   synthetic amorphous fine silica                                                                        1.0%                                                   Example B                                                                      Wettable Powder                                                                Compound 1              65.0%                                                  dodecylphenol polyethylene glycol ether                                                                2.0%                                                   sodium ligninsulfonate  4.0%                                                   sodium silicoaluminate  6.0%                                                   montmorillonite (calcined)                                                                             23.0%                                                  Example C                                                                      Granule                                                                        Compound 1              10.0%                                                  attapulgite granules (low volative                                                                     90.0%                                                  matter, 0.71/0.30 mm; U.S.S. No.                                               25-50 sieves)                                                                  Example D                                                                      Extruded Pellet                                                                Compound 1              25.0%                                                  anhydrous sodium sulfate                                                                               10.0%                                                  crude calcium ligninsulufonate                                                                         5.0%                                                   sodium alkylnaphthalenesulfonate                                                                       1.0%                                                   calcium/magnesium bentonite                                                                            59.0%                                                  ______________________________________                                    

UTILITY

The compounds of the present invention are active postemergence and preemergence herbicides and especially for broadleaf and grass weed control in plantation crops including citrus, sugarcane, coffee, oil palm, rubber, pineapple, grapes, banana and conifers, such as loblolly pine. Most of the plantation crops are very important in mankind's diet while others are sources of useful raw materials. The compounds can be applied as preemergence or postemergence treatments using techniques of banding, directed sprays or broadcast applications. By selecting effective application rates, application techniques and adjuvants, compounds of this invention can be used for selective weed control in plantation crops.

Alternatively, compounds of this invention can be used in areas where complete control of all vegetation is desired, such as around fuel storage tanks, ammunition depots, industrial storage areas, oil well sites, drive-in theaters, around billboards, highways and railroad structures and in fence rows.

Effective application rates for the compounds of this invention are 5 to 5000 g/ha with a preferred rate range of 10 to 2000 g/ha. One skilled in the art can select the effective rates for a given situation.

The compounds of this invention may be used alone or in combination with other commercial herbicides, insecticides or fungicides. The following list exemplifies some of the herbicides suitable for use in mixtures. A combination of a compound from this invention with one or more of the following herbicides may be particularly useful for weed control in plantation crops.

Compounds of this invention can be used alone or in combination with other commercial herbicides, insecticides or fungicides. A mixture of one or more of the following herbicides with a compound of this invention may be particularly useful for weed control. Examples of other herbicides with which compounds of this invention can be formulated are: acetochlor, acifluorfen, acrolein, 2-propenal, alachlor, ametryn, amidosulfuron, ammonium sulfamate, amitrole, anilofos, asulam, atrazine, barban, benefin, bensulfuron methyl, bensulide, bentazon, benzofluor, benzoylprop, bifenox, bromacil, bromoxynil, bromoxynil heptanoate, bromoxynil octanoate, butachlor, buthidazole, butralin, butylate, cacodylic acid, 2-chloro-N,N-di-2-propenylacetamide, 2-chloroallyl diethyldithiocarbamate, chloramben, chlorbromuron, chloridazon, chlorimuron ethyl, chlormethoxynil, chlornitrofen, chloroxuron, chlorpropham, chlorsulfuron, chlortoluron, cinmethylin, cinosulfuron, clethodim, clomazone, cloproxydim, clopyralid, calcium salt of methylarsonic acid, cyanazine, cycloate, cycluron, cyperquat, cyprazine, cyprazole, cypromid, dalapon, dazomet, dimethyl 2,3,5,6-tetrachloro-1,4-benzenedicarboxylate, desmedipham, desmetryn, dicamba, dichlobenil, dichlorprop, diclofop, diethatyl, difenzoquat, diflufenican, dimepiperate, dinitramine, dinoseb, diphenamid, dipropetryn, diquat, diuron, 2-methyl-4,6-dinitrophenol, disodium salt of methylarsonic acid, dymron, endothall, S-ethyl dipropylcarbamothioate, esprocarb, ethalfluralin, ethametsulfuron methyl, ethofumesate, fenac, fenoxaprop, fenuron, salt of fenuron and trichloroacetic acid, flamprop, fluazifop, fluazifop-P, fluchloralin, flumesulam, flumipropyn, fluometuron, fluorochloridone, fluorodifen, fluoroglycofen, flupoxam, fluridone, fluroxypyr, fluzasulfuron, fomesafen, fosamine, glyphosate, haloxyfop, hexaflurate, hexazinone, imazamethabenz, imazapyr, imazaquin, imazamethabenz methyl, imazethapyr, imazosulfuron, ioxynil, isopropalin, isoproturon, isouron, isoxaben, karbutilate, lactofen, lenacil, linuron, metobenzuron, metsulfuron methyl, methylarsonic acid, monoammonium salt of methylarsonic acid, (4-chloro-2-methylphenoxy)acetic acid, S,S'-dimethyl-2-(difluoromethyl)-4-(2-methylpropyl)-6-(trifluoromethyl)-3,5-pyridinedicarbothioate, mecoprop, mefenacet, mefluidide, methalpropalin, methabenzthiazuron, metham, methazole, methoxuron, metolachlor, metribuzin, 1,2-dihydropyridazine-3,6-dione, molinate, monolinuron, monuron, monuron salt and trichloroacetic acid, monosodium salt of methylarsonic acid, napropamide, naptalam, neburon, nicosulfuron, nitralin, nitrofen, nitrofluorfen, norea, norflurazon, oryzalin, oxadiazon, oxyfluorfen, paraquat, pebulate, pendimethalin, perfluidone, phenmedipham, picloram, 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitroacetophenone oxime-O-acetic acid methyl ester, pretilachlor, primisulfuron, procyazine, profluralin, prometon, prometryn, pronamide, propachlor, propanil, propazine, propham, prosulfalin, prynachlor, pyrazolate, pyrazon, pyrazosulfuron ethyl, quinchlorac, quizalofop ethyl, rimsulfuron, secbumeton, sethoxydim, siduron, simazine, 1-(a,a-dimethylbenzyl)-3-(4-methylphenyl)urea, sulfometuron methyl, trichloroacetic acid, tebuthiuron, terbacil, terbuchlor, terbuthylazine, terbutol, terbutryn, thifensulfuron methyl, thiobencarb, triallate, trialkoxydim, triasulfuron, tribenuron methyl, triclopyr, tridiphane, trifluralin, trimeturon, (2,4-dichlorophenoxy)acetic acid, 4-(2,4-dichlorophenoxy)butanoic acid, vernolate, and xylachlor.

In certain instances, combinations with other herbicides having a similar spectrum of control but a different mode of action will be particularly advantageous for resistance management.

A herbicidally effective amount of the compounds of this invention is determined by a number of factors. These factors include: formulation selected, method of application, amount and type of vegetation present, growing conditions, etc. In general, a herbicidally effective amount of a compound(s) of this invention is applied at rates from about 0.001 to 20 kg/ha with a preferred rate range of 0.004 to 0.25 kg/ha. One skilled in the art can easily determine application rates necessary for the desired level of weed control.

The following Tests demonstrate the control efficacy of the compounds of this invention specific weeds. The weed control afforded by the compounds is not limited, however, to these species. See Index Tables IV through VI for compound descriptions.

Selective herbicidal properties of the subject compounds were discovered in greenhouse tests as described below. Test procedures and results follows.

                                      TABLE IV                                     __________________________________________________________________________      ##STR406##                                                                                              m.p.                                                 No.                                                                               R.sup.1 R.sup.2 R.sup.3                                                                           X Y (°C.)                                                                        .sup.1 H-NMR                                    __________________________________________________________________________     1  CH.sub.3                                                                               CH.sub.2 Ph                                                                            CF.sub.3                                                                          Cl                                                                               F 145-147                                                                             7.4 (m, 6H)                                                                    6.85 (d, 1H)                                                                   6.4 (s, 1H)                                                                    5.1 (s, 2H)                                                                    3.55 (s, 3H)                                    2  CH.sub.3                                                                               H       CF.sub.3                                                                          Cl                                                                               F Foam 7.15 (d, 1H)                                                                   6.9 (d, 1H)                                                                    6.4 (s, 1H)                                                                    5.8 (s, 1H)                                                                    3.6 (s, 3H)                                     3  CH.sub.3                                                                                ##STR407##                                                                            CF.sub.3                                                                          Cl                                                                               F Foam                                                                                 ##STR408##                                         ##STR409##                                                                             ##STR410##                                                                            CF.sub.3                                                                          Cl                                                                               F Oil                                                                                  ##STR411##                                     7  CH.sub.2 CHCH.sub.2                                                                    CH.sub.2 CHCH.sub.2                                                                    CF.sub.3                                                                          Cl                                                                               F Oil  7.3 (d, 1H)                                                                    6.8 (d, 1H)                                                                    6.4 (s, 1H)                                                                    6.0 (m, 2H)                                                                    5.4 (m, 4H)                                                                    4.6 (d, 4H)                                     9  CH.sub.3                                                                               CH.sub.2 CHCH.sub.2                                                                    CF.sub.3                                                                          Cl                                                                               F 102-105                                                                             7.3 (d, 1H)                                                                    6.8 (d, 1H)                                                                    6.4 (s, 1H)                                                                    6.0 (m, 1H)                                                                    5.4 (m, 2H)                                                                    4.6 (d, 2H)                                                                    3.6 (s, 3H)                                     __________________________________________________________________________

                                      TABLE V                                      __________________________________________________________________________      ##STR412##                                                                    No.                                                                               R.sup.1                                                                               R.sup.3                                                                           R.sup.4                                                                          R.sup.9 X Y m.p. (°C.)                                                                    .sup.1 H-NMR                                  __________________________________________________________________________     11 CH.sub.3                                                                              CF.sub.3                                                                          H CH.sub.3                                                                               Cl                                                                               F Foam  7.05 (d, 1H)                                                                   6.4 (s, 1H)                                                                    5.1 (m, 1H)                                                                    3.55 (s, 3H)                                                                   3.1 (m, 1H)                                                                    2.8 (m, 1H)                                                                    1.5 (d, 3H)                                   12 CH.sub.3                                                                              CF.sub.3                                                                          H CH.sub.3                                                                               Cl                                                                               Cl                                                                               64-66 7.3 (s, 1H)                                                                    6.4 (s, 1H)                                                                    5.1 (m, 1H)                                                                    3.6 (d, 3H)                                                                    3.25 (m, 1H)                                                                   2.75 (m, 1H)                                                                   1.54 (d, d 3H)                                13                                                                                 ##STR413##                                                                           CF.sub.3                                                                          H CH.sub.3                                                                               Cl                                                                               F Oil                                                                                   ##STR414##                                   14 CH.sub.2 CH.sub.2 CH.sub.2                                                            CF.sub.3                                                                          H CH.sub.3                                                                               Cl                                                                               F Oil   7.05 (d, 1H)                                                                   6.4 (s, 1H)                                                                    5.9 (m, 1H)                                                                    5.3 (m, 2H)                                                                    5.1 (m, 1H)                                                                    4.6 (d, 1H)                                                                    3.2 (m, 1H)                                                                    2.8 (m, 1H)                                                                    1.5 (d, 3H)                                   15 CH.sub.2 Ph                                                                           CF.sub.3                                                                          H CH.sub.3                                                                               Cl                                                                               F Oil   7.2 (m, 7H)                                                                    7.0 (d, 1H)                                                                    6.4 (s, 1H)                                                                    5.2 (d, 2H)                                                                    5.1 (m, 1H)                                                                    3.1 (m, 1H)                                                                    2.7 (m, 1H)                                                                    1.5 (d, 3H)                                   17 CH.sub.3                                                                              CH.sub.3                                                                          H CH.sub.3                                                                               Cl                                                                               F Oil   7.0 (d, 1H)                                                                    5.7 (s, 1H)                                                                    5.0 (m, 1H)                                                                    3.4 (s, 3H)                                                                    3.2 (d, d 1H)                                                                  2.8 (d, d 1H)                                                                  2.3 (s, 3H)                                                                    1.5 (d, 3H)                                   19 CH.sub.2 CH.sub.3                                                                     CH.sub.3                                                                          H CH.sub.3                                                                               Cl                                                                               F 140-142                                                                              7.0 (d, 1H)                                                                    5.68 (s, 1H)                                                                   5.05 (m, 1H)                                                                   3.95 (q, 1H)                                                                   3.2 (qu, 1H)                                                                   2.8 (qu, 1H)                                                                   2.35 (s, 3H)                                                                   1.55 (d, 3H)                                                                   1.3 (t, 3H)                                   20 CH.sub.3                                                                              CF.sub.3                                                                          H CO.sub.2 H                                                                             Cl                                                                               F 190-194                                             21 CH.sub.3                                                                              CF.sub.3                                                                          H CO.sub.2 tBu                                                                           Cl                                                                               F 65-67                                               22 CH.sub.3                                                                              CF.sub.3                                                                          H CO.sub.2 CH.sub.3                                                                      Cl                                                                               F 77-79                                               23 CH.sub.3                                                                              CF.sub.3                                                                          H CO.sub.2 iPr                                                                           Cl                                                                               F 56-59                                               24 CH.sub.3                                                                              CF.sub.3                                                                          H CON(CH.sub.3).sub.2                                                                    Cl                                                                               F 92-94                                               25 CH.sub.3                                                                              CF.sub.3                                                                          H CH.sub.2 OC(O)CH.sub.3                                                                 Cl                                                                               F 58-61                                               __________________________________________________________________________

                                      TABLE VI                                     __________________________________________________________________________      ##STR415##                                                                    No.                                                                               R.sup.1                                                                           R.sup.3                                                                             X Y R.sup.2   m.p. (°C.)                                                                    .sup.1 H-NMR                                    __________________________________________________________________________     5  CH.sub.3                                                                          N(CH.sub.3).sub.2                                                                   Cl                                                                               F H         247-249                                                                              7.45 (d, 1H)                                                                   6.95 (d, 1H)                                                                   3.3 (s, 3H)                                                                    3.0 (s, 6H)                                     6  CH.sub.3                                                                          N(CH.sub.3).sub.2                                                                   Cl                                                                               F CH.sub.2 Ph                                                                              193-194                                                                              7.4 (m, 6H)                                                                    6.95 (d, 1H)                                                                   5.05 (d, 2H)                                                                   3.45 (s, 3H)                                                                   3.1 (s, 6H)                                     8  CH.sub.3                                                                          N(CH.sub.3).sub.2                                                                   Cl                                                                               F                                                                                 ##STR416##                                                                              61-65                                                                                 ##STR417##                                     16 CH.sub.3                                                                          N(CH.sub.3).sub.2                                                                   Cl                                                                               F H         134-135                                                                              7.28 (s, 1H)                                                                   6.84 (d, 1H)                                                                   6.05 (m, 1H)                                                                   5.45 (d, 1H)                                                                   5.3 (d, 1H)                                                                    4.55 (s, 2H)                                                                   3.45 (s, 3H)                                                                   3.12 (s, 6H)                                    18 CH.sub.3                                                                          N(CH.sub.3).sub.2                                                                   Cl                                                                               F CH(CH.sub.3)CH.sub.2                                                                     191-195                                                                              7.3 (d, 1H)                                                                    6.8 (d, 1H)                                                                    6.36 (s, 1H)                                                                   6.0 (m, 1H)                                                                    5.4 (m, 2H)                                                                    4.55 (d, 2H)                                                                   3.56 (s, 3H)                                    __________________________________________________________________________

TEST A

Seeds of barley (Hordeum vulgare), barnyardgrass (Echinochloa crus-galli), bedstraw (Galium aparine), blackgrass (Alopecurus myosuroides), cheatgrass (Bromus secalinus), chickweed (Stellaria media), cocklebur (Xanthium pensylvanicum), corn (Zea mays, cotton (Gossypium hirsutum), crabgrass (Digitaria spp.), giant foxtail (Setaria faberii), lambsquarters (Chenopodium album), morningglory (Ipomoea hederacea), rape (Brassica napus), rice (Oryza sativa), sorghum (Sorghum bicolor), soybean (Glycine max), sugar beet (Beta vulgaris), velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), wild buckwheat (Polygonum convolvulus), and wild oat (Avena fatua) and purple nutsedge (Cyperus rotundus) tubers were planted and treated preemergence with test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species were also treated with postemergence applications of test chemicals. Plants ranged in height from two to eighteen cm (one to four leaf stage) for postemergence treatments. Treated plants and controls were maintained in a greenhouse for twelve to sixteen days, after which all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table A, are based on a scale of 0 to 10 where 0 is no effect and 10 is complete control. A dash (-) response indicates no test result.

                  TABLE A                                                          ______________________________________                                                    COMPOUND                                                            Rate 400 g/ha                                                                               1     2     3   5   6   8   11  16  17  18                        ______________________________________                                         POSTEMERGENCE                                                                  Barley       6     9     10  3   4   5   10  --  6   8                         Barnyardgrass                                                                               9     10    10  5   3   10  10  7   9   10                        Bedstraw     10    10    10  3   4   8   10  --  8   10                        Blackgrass   10    9     10  3   4   5   10  --  5   9                         Cheatgrass   7     8     10  4   4   5   10  --  5   10                        Chickweed    10    10    10  3   4   8   10  --  5   10                        Cocklebur    10    10    10  3   6   8   10  8   7   9                         Corn         6     9     10  2   3   10  10  3   6   9                         Cotton       10    10    10  9   9   10  10  10  10  10                        Crabgrass    5     7     10  3   4   10  10  5   9   9                         Giant foxtail                                                                               8     10    10  3   6   9   10  9   9   10                        Lambsquarter 10    10    10  5   8   10  10  --  10  10                        Morningglory 10    10    10  8   7   9   10  10  9   10                        Nutsedge     5     --    --  1   0   9   7   2   2   5                         Rape         10    7     10  1   5   9   10  --  7   10                        Rice         6     7     10  3   3   9   10  7   9   9                         Sorghum      6     9     10  2   3   6   10  4   9   10                        Soybean      10    10    10  4   6   9   10  9   9   9                         Sugar beet   10    10    10  5   9   10  10  --  10  10                        Velvetleaf   10    10    10  2   9   10  10  10  10  10                        Wheat        5     --    --  3   4   6   10  --  7   10                        Wild buckwheat                                                                              --    --    --  6   6   10  10  --  10  10                        Wild oat     9     9     10  2   4   6   10  --  8   10                        PREEMERGENCE                                                                   Barley       3     3     9   0   0   8   9   --  4   5                         Barnyardgrass                                                                               9     9     10  0   0   9   10  9   10  10                        Bedstraw     10    10    10  3   10  10  10  --  10  9                         Blackgrass   10    7     10  0   5   9   10  --  4   10                        Cheatgrass   10    10    10  0   0   9   10  --  9   10                        Chickweed    10    9     10  0   3   10  10  --  4   9                         Cocklebur    0     7     10  0   0   10  10  6   6   10                        Corn         3     4     10  0   0   6   10  8   8   10                        Cotton       8     8     10  0   0   10  10  6   8   10                        Crabgrass    10    9     10  0   9   10  10  10  10  10                        Giant foxtail                                                                               10    10    10  0   9   10  10  10  10  10                        Lambsquarter 10    10    10  0   10  10  10  --  10  10                        Morningglory 5     10    10  0   0   10  10  10  9   10                        Nutsedge     2     10    10  0   10  1   7   3   4   5                         Rape         10    10    10  1   2   10  10  --  10  10                        Rice         5     3     10  0   0   10  10  6   9   10                        Sorghum      7     9     10  0   0   4   10  8   9   10                        Soybean      3     9     10  0   0   6   10  4   9   9                         Sugar beet   10    10    10  1   9   10  10  --  10  10                        Velvetleaf   10    10    10  0   10  10  10  10  10  10                        Wheat        3     7     10  0   0   9   9   --  6   8                         Wild buckwheat                                                                              10    10    10  0   10  10  10  --  10  10                        Wild oat     9     9     10  0   0   10  10  --  3   10                        ______________________________________                                                    COMPOUND                                                            Rate 200 g/ha                                                                               4            9      12                                            ______________________________________                                         POSTEMERGENCE                                                                  Barley       5            7      7                                             Barnyardgrass                                                                               10           10     6                                             Bedstraw     9            10     9                                             Blackgrass   6            9      4                                             Cheatgrass   7            9      5                                             Chickweed    10           10     6                                             Cocklebur    7            10     7                                             Corn         9            9      7                                             Cotton       10           10     10                                            Crabgrass    9            10     7                                             Giant foxtail                                                                               9            10     8                                             Lambsquarter 10           10     10                                            Morningglory 9            10     9                                             Nutsedge     5            5      1                                             Rape         10           10     9                                             Rice         10           9      9                                             Sorghum      9            9      9                                             Soybean      9            9      10                                            Sugar beet   10           10     10                                            Velvetleaf   10           10     8                                             Wheat        7            6      7                                             Wild buckwheat                                                                              10           10     10                                            Wild oat     9            10     8                                             PREEMERGENCE                                                                   Barley       2            6      1                                             Barnyardgrass                                                                               10           10     9                                             Bedstraw     9            10     10                                            Blackgrass   9            10     8                                             Cheatgrass   9            10     3                                             Chickweed    10           10     1                                             Cocklebur    6            10     7                                             Corn         9            9      9                                             Cotton       7            9      3                                             Crabgrass    10           10     10                                            Giant foxtail                                                                               10           10     10                                            Lambsquarter 10           10     10                                            Morningglory 10           10     10                                            Nutsedge     10           2      0                                             Rape         8            10     10                                            Rice         9            9      8                                             Sorghum      9            10     7                                             Soybean      9            10     8                                             Sugar beet   9            10     10                                            Velvetleaf   10           10     10                                            Wheat        7            9      2                                             Wild buckwheat                                                                              10           10     10                                            Wild oat     8            10     6                                             ______________________________________                                                    COMPOUND                                                            Rate 100 g/ha                                                                               1     2     3   5   6   8   11  16  17  18                        ______________________________________                                         POSTEMERGENCE                                                                  Barley       5     5     7   3   3   5   7   --  4   7                         Barnyardgrass                                                                               8     7     10  1   2   4   10  3   8   9                         Bedstraw     8     9     10  2   3   5   10  --  7   9                         Blackgrass   6     5     10  2   2   5   10  --  4   6                         Cheatgrass   6     5     9   1   3   4   10  --  3   5                         Chickweed    --    --    10  2   2   6   10  --  4   8                         Cocklebur    8     6     10  2   4   6   10  7   6   8                         Corn         5     3     9   2   2   7   9   3   4   6                         Cotton       10    10    10  9   10  10  10  10  10  10                        Crabgrass    4     2     10  2   --  7   10  2   5   8                         Giant foxtail                                                                               5     9     10  2   5   7   10  4   7   8                         Lambsquarter 10    10    10  3   7   9   10  --  10  10                        Morningglory 10    10    10  5   7   9   10  8   8   10                        Nutsedge     5     2     --  0   0   --  8   0   2   3                         Rape         10    3     10  1   2   7   10  --  5   9                         Rice         5     6     9   3   3   6   10  4   9   8                         Sorghum      5     4     9   1   2   5   10  4   5   8                         Soybean      8     8     10  3   5   8   9   8   9   9                         Sugar beet   10    10    10  3   7   10  10  --  9   10                        Velvetleaf   10    10    10  2   6   7   10  10  9   10                        Wheat        4     4     9   3   2   4   8   --  5   9                         Wild buckwheat                                                                              --    --    10  3   3   10  10  --  9   9                         Wild oat     7     5     9   3   3   4   9   --  6   9                         PREEMERGENCE                                                                   Barley       0     0     4   0   0   1   8   --  0   2                         Barnyardgrass                                                                               8     3     10  0   0   3   10  2   8   9                         Bedstraw     10    5     10  0   0   2   10  --  4   8                         Blackgrass   9     3     10  0   0   5   10  --  2   6                         Cheatgrass   5     2     8   0   0   4   10  --  1   8                         Chickweed    10    --    10  0   2   5   10  --  2   9                         Cocklebur    0     0     10  0   0   2   10  2   2   5                         Corn         3     0     9   0   0   0   9   1   2   7                         Cotton       0     0     10  0   0   1   10  2   4   10                        Crabgrass    9     6     10  0   9   10  10  2   9   9                         Giant foxtail                                                                               9     10    10  0   0   2   10  5   5   10                        Lambsquarter 10    10    10  0   10  10  10  --  10  9                         Morningglory 0     2     10  0   0   3   10  6   4   10                        Nutsedge     0     8     7   0   0   0   5   2   1   4                         Rape         10    3     10  0   0   9   10  --  6   9                         Rice         1     1     9   0   0   6   9   3   4   8                         Sorghum      3     1     9   0   0   3   10  1   1   6                         Soybean      1     2     9   0   0   2   10  1   8   5                         Sugar beet   5     7     10  0   0   7   10  --  9   9                         Velvetleaf   2     10    10  0   0   10  10  6   10  10                        Wheat        0     1     8   0   0   1   7   --  0   4                         Wild buckwheat                                                                              10    0     10  0   0   8   10  --  10  9                         Wild oat     7     3     9   0   0   0   9   --  0   5                         ______________________________________                                                    COMPOUND                                                            Rate 50 g/ha 4            9      12                                            ______________________________________                                         POSTEMERGENCE                                                                  Barley       4            5      5                                             Barnyardgrass                                                                               7            9      4                                             Bedstraw     9            10     6                                             Blackgrass   4            6      2                                             Cheatgrass   5            6      3                                             Chickweed    10           10     3                                             Cocklebur    6            10     4                                             Corn         5            7      4                                             Cotton       9            10     9                                             Crabgrass    6            9      5                                             Giant foxtail                                                                               7            9      7                                             Lambsquarter 10           10     9                                             Morningglory 8            10     6                                             Nutsedge     5            3      1                                             Rape         10           10     5                                             Rice         8            8      7                                             Sorghum      7            8      5                                             Soybean      9            9      6                                             Sugar beet   10           10     9                                             Velvetleaf   8            10     5                                             Wheat        5            7      3                                             Wild buckwheat                                                                              10           10     9                                             Wild oat     5            7      4                                             PREEMERGENCE                                                                   Barley       0            2      0                                             Barnyardgrass                                                                               7            9      7                                             Bedstraw     10           10     8                                             Blackgrass   5            9      5                                             Cheatgrass   5            8      2                                             Chickweed    10           10     0                                             Cocklebur    0            9      0                                             Corn         5            9      6                                             Cotton       2            7      2                                             Crabgrass    9            10     10                                            Giant foxtail                                                                               8            10     9                                             Lambsquarter 10           10     10                                            Morningglory 2            10     5                                             Nutsedge     5            3      0                                             Rape         2            10     7                                             Rice         2            9      7                                             Sorghum      3            9      6                                             Soybean      2            10     5                                             Sugar beet   9            10     10                                            Velvetleaf   9            10     9                                             Wheat        0            7      1                                             Wild buckwheat                                                                              9            10     5                                             Wild oat     5            8      1                                             ______________________________________                                    

TEST B

The compounds evaluated in this test were formulated in a non-phytoxic solvent and applied to the soil surface before plant seedlings emerged (preemergence application), to water that covered the soil surface (flood application), and to plants that were in the one-to-four leaf stage (postemergence application). A sandy loam soil was used for the preemergence and postemergence tests, while a silt loam soil was used in the flood test. Water depth was approximately 2.5 cm for the flood test and was maintained at this level for the duration of the test.

Plant species in the preemergence and postemergence tests consisted of barley (Hordeum vulgare), bedstraw (Galium aparine), blackgrass (Alopecurus myosuroides), chickweed (Stellaria media), corn (Zea mays), cotton (Gossypium hirsutum), crabgrass (Digitaria sanguinalis), downy brome (Bromus tectorum), giant foxtail (Setaria faberii), lambsquarters (Chenopodium album), morningglory (Ipomoea hederacea), pigweed (Amaranthusretroflexus), rape (Brassica napus), ryegrass (Lolium multiflorum), sorghum (Sorghum bicolor), soybean (Glycine max), speedwell (Veronica persica), sugar beet (Beta vulgaris), velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), wild buckwheat (Polygonum convolvulus), and wild oat (Avena fatua).

All plant species were planted one day before application of the compound for the preemergence portion of this test. Plantings of these species were adjusted to produce plants of appropriate size for the post-emergence portion of the test. Plant species in the flood test consisted of barnyardgrass (Echinochloa crus-galli), rice (Oryza sativa), umbrella sedge (Cyperus difformis) and duck salad (Heteranthera limosa). All plant species were grown using normal greenhouse practices. Visual evaluations of injury expressed on treated plants, when compared to untreated controls, were recorded approximately fourteen to twenty one days after application of the test compound. Plant response ratings, summarized in Table B, were recorded on a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash (-) response indicates no test result.

                  TABLE B                                                          ______________________________________                                                      COMPOUND                                                          Rate 250 g/ha                                                                               4                                                                 ______________________________________                                         POSTEMERGENCE                                                                  Barley Igri   70                                                               Barnyard 2 leaf                                                                             --                                                                Barnyardgrass                                                                               100                                                               Bedstraw     100                                                               Blackgrass   100                                                               Chickweed    100                                                               Corn          90                                                               Cotton       100                                                               Crabgrass    100                                                               Downy Brome  100                                                               Duck salad    15                                                               Giant foxtail                                                                               100                                                               Lambsquarters                                                                               100                                                               Morningglory 100                                                               Pigweed      100                                                               Rape         100                                                               Rice Japonica                                                                               100                                                               Ryegrass      90                                                               Sorghum      100                                                               Soybean      100                                                               Speedwell    --                                                                Sugar beet   100                                                               Umbrella sedge                                                                               10                                                               Velvetleaf   100                                                               Wheat         90                                                               Wild buckwheat                                                                              100                                                               Wild oat      90                                                               PREEMERGENCE                                                                   Barley Igri   50                                                               Bedstraw     100                                                               Blackgrass   100                                                               Chickweed    100                                                               Corn         100                                                               Cotton       100                                                               Crabgrass    100                                                               Downy Brome   95                                                               Giant foxtail                                                                               100                                                               Lambsquarters                                                                               10)                                                               Morningglory 100                                                               Pigweed      100                                                               Rape         100                                                               Ryegrass     100                                                               Sorghum      100                                                               Soybean      100                                                               Speedwell    --                                                                Sugar beet   100                                                               Velvetleaf   100                                                               Wheat         90                                                               Wild buckwheat                                                                              100                                                               Wild oat      95                                                               ______________________________________                                                    COMPOUND                                                            Rate 125 g/ha                                                                               1        3      4      9    12                                    ______________________________________                                         POSTEMERGENCE                                                                  Barley Igri   0       100     60     95  --                                    Barnyard 2 leaf                                                                             --       --     --     --   --                                    Barnyardgrass                                                                               100      100    100    100  100                                   Bedstraw     100      100    100    100  --                                    Blackgrass    50      100    100    100  --                                    Chickweed    100      100    100    100  --                                    Corn          25       98     90     98  --                                    Cotton       100      100    100    100  --                                    Crabgrass     50      100     95    100  --                                    Downy Brome   0       100     85    100  --                                    Duck salad    0        90     0      95   30                                   Giant foxtail                                                                               100      100    100    100  --                                    Lambsquarters                                                                               100      100    100    100  --                                    Morningglory 100      100    100    100  --                                    Pigweed      100      100    100    100  --                                    Rape         100      100    100    100  --                                    Rice Japonica                                                                                95      100    100    100   95                                   Ryegrass      40      100     70    100  --                                    Sorghum       60      100     90    100  --                                    Soybean       98      100     90    100  --                                    Speedwell    100      100    --     100  --                                    Sugar beet   100      100    100    100  --                                    Umbrella sedge                                                                              100      100     0     100   85                                   Velvetleaf   100      100    100    100  --                                    Wheat         0       100     60     95  --                                    Wild buckwheat                                                                              100      100    100    100  --                                    Wild oat      40      100     80     95  --                                    ______________________________________                                                      COMPOUND                                                          Rate 125 g/ha  1      3         4    12                                        ______________________________________                                         PREEMERGENCE                                                                   Barley Igri     0     100        30   50                                       Bedstraw       100    100       100  100                                       Blackgrass      30    100        90   90                                       Chickweed      100    100       100   0                                        Corn            50    100        70   90                                       Cotton          70    100       100   10                                       Crabgrass      100    100       100  100                                       Downy Brome     0     100        90   50                                       Giant foxtail  100    100       100  100                                       Lambsquarters  100    100       100  100                                       Morningglory   100    100       100  100                                       Pigweed        100    100       100  100                                       Rape           100    100       100  100                                       Ryegrass        20    100        95   90                                       Sorghum         60    100        90  100                                       Soybean        100    100       100  100                                       Speedwell      100    100       --   100                                       Sugar beet     100    100       100  100                                       Velvetleaf     100    100       100  100                                       Wheat           0     100        85  100                                       Wild buckwheat 100    100       100  100                                       Wild oat        0     100        75   90                                       ______________________________________                                                      COMPOUND                                                          Rate 62 g/ha   1      3         4    11                                        ______________________________________                                         POSTEMERGENCE                                                                  Barley Igri     0      95        50   90                                       Barnyard 2 leaf                                                                               --     --        100  --                                        Barnyardgrass  100    100       100  100                                       Bedstraw       100    100       100  100                                       Blackgrass      50    100        95  100                                       Chickweed      100    100       100  100                                       Corn            20     98        80  100                                       Cotton         100    100       100  100                                       Crabgrass       20    100        90  100                                       Downy Brome     0     100        75   90                                       Duck salad      0      90        0    90                                       Giant foxtail   80    100        95  100                                       Lambsquarters  100    100       100  100                                       Morningglory   100    100       100  100                                       Pigweed        100    100       100  100                                       Rape           100    100       100  100                                       Rice Japonica   90    100        95  100                                       Ryegrass        40    100        70   90                                       Sorghum         30    100        85  100                                       Soybean         98    100       100  100                                       Speedwell      100    100       100  --                                        Sugar beet     100    100       100  100                                       Umbrella sedge  90    100        0    90                                       Velvetleaf     100    100       100  100                                       Wheat           0     100        60   90                                       Wild buckwheat 100    100       100  100                                       Wild oat        40    100        60   95                                       PREEMERGENCE                                                                   Barley Igri     0     100        60   90                                       Bedstraw       100    100       100  100                                       Blackgrass     --     100        85  100                                       Chickweed      100    100       100  100                                       Corn            0     100        70  100                                       Cotton          0      98       100  100                                       Crabgrass       80    100       100  100                                       Downy Brome     0     100        75  100                                       Giant foxtail  100    100       100  100                                       Lambsquarters  100    100       100  100                                       Morningglory   100    100       100  100                                       Pigweed        100    100       100  100                                       Rape            50    100       100  100                                       Ryegrass        0     100        95  100                                       Sorghum         50    100        80  100                                       Soybean         30    100        70  100                                       Speedwell      100    100       100  --                                        Sugar beet     100    100       100  100                                       Velvetleaf     100    100       100  100                                       Wheat           0     100       100  100                                       Wild buckwheat 100    100       100  100                                       Wild oat        0     100        70  100                                       ______________________________________                                                    COMPOUND                                                            Rate 31 g/ha 1        3      4      9    12                                    ______________________________________                                         POSTEMERGENCE                                                                  Barley Igri   0        90     40     80  --                                    Barnyard 2 leaf                                                                             --       --     --     --   --                                    Barnyardgrass                                                                               100      100     95    100   70                                   Bedstraw     100      100    100    100  --                                    Blackgrass    30      100     60     80  --                                    Chickweed     90      100    100    100  --                                    Corn          20       70     60     90  --                                    Cotton       100      100    100    100  --                                    Crabgrass     0       100     70     90  --                                    Downy Brome   0       100     50     80  --                                    Duck salad    0        75     0      95   0                                    Giant foxtail                                                                                20      100     75     98  --                                    Lambsquarters                                                                               100      100    100    100  --                                    Morningglory 100      100     90    100  --                                    Pigweed      100      100    100    100  --                                    Rape         100      100    100    100  --                                    Rice Japonica                                                                                75      100     90    100   90                                   Ryegrass      30      100     60     95  --                                    Sorghum       20      100     70     95  --                                    Soybean       80      100     90    100  --                                    Speedwell    100      100    --     100  --                                    Sugar beet   100      100    100    100  --                                    Umbrella sedge                                                                               0        85     0     100   80                                   Velvetleaf   100      100    100    100  --                                    Wheat         0       100     50     50  --                                    Wild buckwheat                                                                              100      100    100    100  --                                    Wild oat      0       100     50     50  --                                    ______________________________________                                                      COMPOUND                                                          Rate 31 g/ha   1      3         4    12                                        ______________________________________                                         PREEMERGENCE                                                                   Barley Igri     0      90        0    20                                       Bedstraw       100    100       100   90                                       Blackgrass      0     100        70   40                                       Chickweed      100    100       100   0                                        Corn            0     100        40   60                                       Cotton          0      98        20   0                                        Crabgrass       80    100       100   98                                       Downy Brome     0     100        40   20                                       Giant foxtail   80    100        95  100                                       Lambsquarters  100    100       100  100                                       Morningglory    30    100       100   50                                       Pigweed        100    100       100  100                                       Rape            20    100        40   50                                       Ryegrass        0     100        80   50                                       Sorghum         30    100        70   90                                       Soybean         20    100        70   40                                       Speedwell      100    100       --   100                                       Sugar beet     100    100       100  100                                       Velvetleaf     100    100       100  100                                       Wheat           0     100        40   50                                       Wild buckwheat 100    100       100   80                                       Wild oat        0     100        30   30                                       ______________________________________                                                      COMPOUND                                                          Rate 16 g/ha   1      3         4    11                                        ______________________________________                                         POSTEMERGENCE                                                                  Barley Igri     0      30        30   70                                       Barnyard 2 leaf                                                                               --     --         70  --                                        Barnyardgrass  100    100       --   100                                       Bedstraw       100    100       100  100                                       Blackgrass      0     100        40   95                                       Chickweed       90    100       --   100                                       Corn            10     60        40   80                                       Cotton         100    100       100  100                                       Crabgrass       0      70        30   70                                       Downy Brome     0      90        50   70                                       Duck salad      0      70        0    70                                       Giant foxtail   0     100        50   90                                       Lambsquarters   90    100       --   100                                       Morningglory   100    100        50  100                                       Pigweed        100    100       100  100                                       Rape           100    100        80  100                                       Rice Japonica   65    100        70   95                                       Ryegrass        0     100        40   90                                       Sorghum         0      98        50   90                                       Soybean         70    100        60   90                                       Speedwell      100    100       100  --                                        Sugar beet     100    100       100  100                                       Umbrella sedge  0      55        0    75                                       Velvetleaf     100    100       100  100                                       Wheat           0      60        30   90                                       Wild buckwheat 100    100       100  100                                       Wild oat        0      60        40   85                                       PREEMERGENCE                                                                   Barley Igri     0      50        0    70                                       Bedstraw       100    100       100  100                                       Blackgrass     --     100        50   90                                       Chickweed       80    100       100   90                                       Corn            0      80        0    90                                       Cotton          0      98        0   100                                       Crabgrass       50    100        50  100                                       Downy Brome     0      90        10   90                                       Giant foxtail   80    100        60  100                                       Lambsquarters   95    100       100  100                                       Morningglory    0     100        10  100                                       Pigweed        100    100       100  100                                       Rape            20    100        30  100                                       Ryegrass        0     100        60   95                                       Sorghum         20    100        10  100                                       Soybean         0     100        0   100                                       Speedwell      100    100       100  --                                        Sugar beet      80    100        90  100                                       Velvetleaf      95    100       100  100                                       Wheat           0      60        0    90                                       Wild buckwheat 100    100       100  100                                       Wild oat        0      95        0    90                                       ______________________________________                                                   COMPOUND                                                             Rate 8 g/ha  9           12                                                    ______________________________________                                         POSTEMERGENCE                                                                  Barley Igri   60         --                                                    Barnyard 2 leaf                                                                             --          --                                                    Barnyardgrass                                                                               100         20                                                    Bedstraw     100         --                                                    Blackgrass    50         --                                                    Chickweed    100         --                                                    Corn          60         --                                                    Cotton       100         --                                                    Crabgrass     60         --                                                    Downy Brome   50         --                                                    Duck salad    80          0                                                    Giant foxtail                                                                                80         --                                                    Lambsquarters                                                                               100         --                                                    Morningglory 100         --                                                    Pigweed      100         --                                                    Rape          90         --                                                    Rice Japonica                                                                                95         45                                                    Ryegrass      50         --                                                    Sorghum       70         --                                                    Soybean      100         --                                                    Speedwell    100         --                                                    Sugar beet   100         --                                                    Umbrella sedge                                                                               90          0                                                    Velvetleaf   100         --                                                    Wheat         30         --                                                    Wild buckwheat                                                                              100         --                                                    Wild oat      30         --                                                    ______________________________________                                                      COMPOUND                                                          Rate 8 g/ha  12                                                                ______________________________________                                         PREEMERGENCE                                                                   Barley Igri   0                                                                Bedstraw     20                                                                Blackgrass   20                                                                Chickweed     0                                                                Corn         20                                                                Cotton        0                                                                Crabgrass    50                                                                Downy Brome   0                                                                Giant foxtail                                                                               60                                                                Lambsquarters                                                                               70                                                                Morningglory 20                                                                Pigweed      100                                                               Rape         20                                                                Ryegrass     20                                                                Sorghum      20                                                                Soybean      20                                                                Speedwell    70                                                                Sugar beet   20                                                                Velvetleaf   100                                                               Wheat        20                                                                Wild buckwheat                                                                              30                                                                Wild oat     20                                                                ______________________________________                                                      COMPOUND                                                          Rate 4 g/ha  3           4     11                                              ______________________________________                                         POSTEMERGENCE                                                                  Barley Igri  --          20    40                                              Barnyard 2 leaf                                                                             --          20    --                                              Barnyardgrass                                                                               50          --    80                                              Bedstraw     --          70    80                                              Blackgrass   --          40    50                                              Chickweed    --          --    60                                              Corn         --          30    50                                              Cotton       --          60    100                                             Crabgrass    --          20    50                                              Downy Brome  --          30    50                                              Duck salad    0           0     0                                              Giant foxtail                                                                               --          30    60                                              Lambsquarters                                                                               --          --    100                                             Morningglory --          50    90                                              Pigweed      --          30    60                                              Rape         --          50    80                                              Rice Japonica                                                                               25          35    90                                              Ryegrass     --          30    75                                              Sorghum      --          40    50                                              Soybean      --          40    80                                              Speedwell    --          70    --                                              Sugar beet   --          90    85                                              Umbrella sedge                                                                               0           0    30                                              Velvetleaf   --          30    100                                             Wheat        --          30    50                                              Wild buckwheat                                                                              --          60    90                                              Wild oat     --          20    60                                              ______________________________________                                                         COMPOUND                                                       Rate 4 g/ha       4      11                                                    ______________________________________                                         PREEMERGENCE                                                                   Barley Igri        0     30                                                    Bedstraw          20     100                                                   Blackgrass        10     30                                                    Chickweed         70     70                                                    Corn               0     60                                                    Cotton             0     80                                                    Crabgrass          0     85                                                    Downy Brome        0     50                                                    Giant foxtail     20     90                                                    Lambsquarters     50     100                                                   Morningglory       0     30                                                    Pigweed           100    100                                                   Rape               0     70                                                    Ryegrass           0     60                                                    Sorghum            0     60                                                    Soybean            0     60                                                    Speedwell         30     --                                                    Sugar beet         0     95                                                    Velvetleaf        20     100                                                   Wheat              0     40                                                    Wild buckwheat     0     100                                                   Wild oat           0     50                                                    ______________________________________                                                         COMPOUND                                                       Rate 2 g/ha       9      12                                                    ______________________________________                                         POSTEMERGENCE                                                                  Barley Igri       30     --                                                    Barnyard 2 leaf   --     --                                                    Barnyardgrass     85      0                                                    Bedstraw          100    --                                                    Blackgrass        40     --                                                    Chickweed         100    --                                                    Corn              40     --                                                    Cotton            90     --                                                    Crabgrass         40     --                                                    Downy Brome       30     --                                                    Duck salad        30      0                                                    Giant foxtail     50     --                                                    Lambsquarters     100    --                                                    Morningglory      70     --                                                    Pigweed           100    --                                                    Rape              60     --                                                    Rice Japonica     80     20                                                    Ryegrass          30     --                                                    Sorghum           50     --                                                    Soybean           80     --                                                    Speedwell         100    --                                                    Sugar beet        85     --                                                    Umbrella sedge    90      0                                                    Velvetleaf        100    --                                                    Wheat             25     --                                                    Wild buckwheat    100    --                                                    Wild oat          25     --                                                    ______________________________________                                                      COMPOUND                                                          Rate 2 g/ha  12                                                                ______________________________________                                         PREEMERGENCE                                                                   Barley Igri  0                                                                 Bedstraw     0                                                                 Blackgrass   0                                                                 Chickweed    0                                                                 Corn         0                                                                 Cotton       0                                                                 Crabgrass    20                                                                Downy Brome  0                                                                 Giant foxtail                                                                               20                                                                Lambsquarters                                                                               0                                                                 Morningglory 20                                                                Pigweed      20                                                                Rape         0                                                                 Ryegrass     0                                                                 Sorghum      0                                                                 Soybean      0                                                                 Speedwell    0                                                                 Sugar beet   0                                                                 Velvetleaf   20                                                                Wheat        0                                                                 Wild buckwheat                                                                              20                                                                Wild oat     0                                                                 ______________________________________                                                    COMPOUND                                                            Rate 1 g/ha  3           4     11                                              ______________________________________                                         POSTEMERGENCE                                                                  Barley Igri  --          10    20                                              Barnyard 2 leaf                                                                             --          10    --                                              Barnyardgrass                                                                               20          --     0                                              Bedstraw     --          30    70                                              Blackgrass   --          20    30                                              Chickweed    --          --    30                                              Corn         --          20    30                                              Cotton       --          20    90                                              Crabgrass    --          10    10                                              Downy Brome  --          10    20                                              Duck salad    0           0     0                                              Giant foxtail                                                                               --          20    20                                              Lambsquarters                                                                               --          --    100                                             Morningglory --          40    85                                              Pigweed      --          30    60                                              Rape         --          10    40                                              Rice Japonica                                                                                0          20    45                                              Ryegrass     --          10    30                                              Sorghum      --          20    20                                              Soybean      --          20    50                                              Speedwell    --          10    --                                              Sugar beet   --          40    70                                              Umbrella sedge                                                                               0           0    20                                              Velvetleaf   --          20    60                                              Wheat        --          10    20                                              Wild buckwheat                                                                              --          20    50                                              Wild oat     --          10    20                                              ______________________________________                                                         COMPOUND                                                       Rate 1 g/ha       4      11                                                    ______________________________________                                         PREEMERGENCE                                                                   Barley Igri       0      0                                                     Bedstraw          0      10                                                    Blackgrass        0      0                                                     Chickweed         0      70                                                    Corn              0      0                                                     Cotton            0      10                                                    Crabgrass         0      10                                                    Downy Brome       0      0                                                     Giant foxtail     10     20                                                    Lambsquarters     0      100                                                   Morningglory      0      10                                                    Pigweed           60     50                                                    Rape              0      0                                                     Ryegrass          0      10                                                    Sorghum           0      0                                                     Soybean           0      0                                                     Speedwell         0      --                                                    Sugar beet        0      20                                                    Velvetleaf        --     100                                                   Wheat             0      0                                                     Wild buckwheat    0      60                                                    Wild oat          0      10                                                    ______________________________________                                    

TEST C

Compounds evaluated in this test were formulated in a non-phytoxic solvent and applied to the soil surface before plant seedlings emerged (preemergence application) and to plants that were in the one-to-four leaf stage (postemergence application). A sandy loam soil was used for the preemergence test while a mixture of sandy loam soil and greenhouse potting mix in a 60:40 ratio was used for the postemergence test. Test compounds were applied within approximately one day after planting seeds for the preemergence test.

Plantings of these crops and weed species were adjusted to produce plants of appropriate size for the postemergence test. All plant species were grown using normal greenhouse practices. Crop and weed species include winter barley (Hordeum vulgare cv. `Igri`), blackgrass (Alopecurus myosuroides), chickweed (Stellaria media), downy brome (Bromus tectorum), field violet (Viola arvensis), galium (Galium aparine), green foxtail (Setaria viridis), kochia (Kochia scoparia), lambsquarters (Chenopodium album), speedwell (Veronica persica), rape (Brassica napus), ryegrass (Lolium multiflorum), sugar beet (Beta vulgaris cv. `US1`), sunflower (Helianthus annuus cv. `Russian Giant`), spring wheat (Triticum aestivum cv. `ERA`), winter wheat (Triticum aestivum cv. `Talent`), wild buckwheat (Polygonum convolvulus), wild mustard (Sinapis arvensis), wild oat (Avena fatua), and wild radish (Raphanus raphanistrum).

Blackgrass, galium and wild oat were treated at two growth stages. The first stage (1) was when the plants had two to three leaves. The second stage (2) was when the plants had approximately four leaves or in the initial stages of tillering. Treated plants and untreated controls were maintained in a greenhouse for approximately 21 to 28 days, after which all treated plants were compared to untreated controls and visually evaluated. Plant response ratings, summarized in Table C, are based upon a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash response (-) indicates no test result.

                  TABLE C                                                          ______________________________________                                                          COMPOUND                                                      Rate 125 g/ha    12                                                            ______________________________________                                         PREEMERGENCE                                                                   Blackgrass (1)    30                                                           Blackgrass (2)    30                                                           Chickweed         0                                                            Downy brome       40                                                           Field violet     100                                                           Galium (1)       100                                                           Galium (2)       100                                                           Green foxtail    100                                                           Kochia           100                                                           Lambsquarters    100                                                           Persn Speedwell  100                                                           Rape              80                                                           Ryegrass          90                                                           Sugar beet       100                                                           Sunflower         25                                                           Wheat (Spring)    50                                                           Wheat (Winter)    60                                                           Wild buckwheat   100                                                           Wild mustard     100                                                           Wild oat (1)      80                                                           Wild oat (2)      90                                                           Wild radish      100                                                           Winter Barley     50                                                           ______________________________________                                                          COMPOUND                                                      Rate 64 g/ha     1                                                             ______________________________________                                         POSTEMERGENCE                                                                  Blackgrass (1)    0                                                            Blackgrass (2)    0                                                            Chickweed        55                                                            Downy brome       0                                                            Field violet     100                                                           Galium (1)       94                                                            Galium (2)       100                                                           Green foxtail    35                                                            Kochia           90                                                            Lambsquarters    --                                                            Persn Speedwell  70                                                            Rape             90                                                            Ryegrass         60                                                            Sugar beet       100                                                           Sunflower        55                                                            Wheat (Spring)    0                                                            Wheat (Winter)    0                                                            Wild buckwheat   100                                                           Wild mustard     100                                                           Wild oat (1)      0                                                            Wild oat (2)      0                                                            Wild radish      85                                                            Winter Barley     0                                                            ______________________________________                                                           COMPOUND                                                     Rate 64 g/ha        1      12                                                  ______________________________________                                         PREEMERGENCE                                                                   Blackgrass (1)       20     10                                                 Blackgrass (2)       20     20                                                 Chickweed           100     0                                                  Downy brome          20     20                                                 Field violet         80    100                                                 Galium (1)          100    100                                                 Galium (2)          100    100                                                 Green foxtail       100    100                                                 Kochia              100     90                                                 Lambsquarters       --     100                                                 Persn Speedwell     100    100                                                 Rape                 65     60                                                 Ryegrass             85     60                                                 Sugar beet          100    100                                                 Sunflower            25     20                                                 Wheat (Spring)       0      40                                                 Wheat (Winter)       0      45                                                 Wild buckwheat      100    100                                                 Wild mustard        100    100                                                 Wild oat (1)         25     50                                                 Wild oat (2)         30     55                                                 Wild radish          60     80                                                 Winter Barley        0      30                                                 ______________________________________                                                           COMPOUND                                                     Rate 32 g/ha        1      9                                                   ______________________________________                                         POSTEMERGENCE                                                                  Blackgrass (1)       0      40                                                 Blackgrass (2)       0      50                                                 Chickweed           25     100                                                 Downy brome          0      40                                                 Field violet        100    100                                                 Galium (1)          60     100                                                 Galium (2)          65     100                                                 Green foxtail        0     100                                                 Kochia              60     100                                                 Lambsquarters       --     100                                                 Persn Speedwell     55     100                                                 Rape                50     100                                                 Ryegrass            30     100                                                 Sugar beet          100    100                                                 Sunflower           30      60                                                 Wheat (Spring)       0      55                                                 Wheat (Winter)       0      40                                                 Wild buckwheat      95     100                                                 Wild mustard        90     100                                                 Wild oat (1)         0      60                                                 Wild oat (2)         0      80                                                 Wild radish         50     --                                                  Winter Barley        0      40                                                 ______________________________________                                                           COMPOUND                                                     Rate 32 g/ha        1      12                                                  ______________________________________                                         PREEMERGENCE                                                                   Blackgrass (1)       0      0                                                  Blackgrass (2)       0      0                                                  Chickweed           85      0                                                  Downy brome          0     20                                                  Field violet        60     80                                                  Galium (1)          75     80                                                  Galium (2)          70     100                                                 Green foxtail       100    --                                                  Kochia              90     90                                                  Lambsquarters       --     100                                                 Persn Speedwell     90     100                                                 Rape                35      0                                                  Ryegrass            70     10                                                  Sugar beet          95     100                                                 Sunflower            0      0                                                  Wheat (Spring)       0     20                                                  Wheat (Winter)       0     25                                                  Wild buckwheat      85     100                                                 Wild mustard        70     100                                                 Wild oat (1)         0     20                                                  Wild oat (2)         0     40                                                  Wild radish         45     50                                                  Winter Barley        0     25                                                  ______________________________________                                                           COMPOUND                                                     Rate 16 g/ha        1      9                                                   ______________________________________                                         POSTEMERGENCE                                                                  Blackgrass (1)       0      35                                                 Blackgrass (2)       0      20                                                 Chickweed            0     100                                                 Downy brome          0      40                                                 Field violet        75     100                                                 Galium (1)          30     100                                                 Galium (2)          30     100                                                 Green foxtail        0     100                                                 Kochia              20     100                                                 Lambsquarters       --     100                                                 Persn Speedwell     30     100                                                 Rape                25      80                                                 Ryegrass             0      70                                                 Sugar beet          90     100                                                 Sunflower            0     --                                                  Wheat (Spring)       0      50                                                 Wheat (Winter)       0      30                                                 Wild buckwheat      65     100                                                 Wild mustard        55     100                                                 Wild oat (1)         0      60                                                 Wild oat (2)         0      60                                                 Wild radish         25     100                                                 Winter Barley        0      40                                                 ______________________________________                                                           COMPOUND                                                     Rate 16 g/ha        1      12                                                  ______________________________________                                         PREEMERGENCE                                                                   Blackgrass (1)       0      0                                                  Blackgrass (2)       0      0                                                  Chickweed           55      0                                                  Downy brome          0     10                                                  Field violet        30     40                                                  Galium (1)          50     30                                                  Galium (2)          45     40                                                  Green foxtail       80     70                                                  Kochia              60      0                                                  Lambsquarters       --     80                                                  Persn Speedwell     45     100                                                 Rape                 0      0                                                  Ryegrass            40      0                                                  Sugar beet          65     100                                                 Sunflower            0      0                                                  Wheat (Spring)       0     10                                                  Wheat (Winter)       0     10                                                  Wild buckwheat      60     70                                                  Wild mustard        50     70                                                  Wild oat (1)         0      0                                                  Wild oat (2)         0     30                                                  Wild radish         20      0                                                  Winter Barley        0     10                                                  ______________________________________                                                           COMPOUND                                                     Rate 8 g/ha         1      9                                                   ______________________________________                                         POSTEMERGENCE                                                                  Blackgrass (1)       0      35                                                 Blackgrass (2)       0      0                                                  Chickweed            0     100                                                 Downy brome          0      40                                                 Field violet        35     100                                                 Galium (1)           0     100                                                 Galium (2)           0     100                                                 Green foxtail        0      75                                                 Kochia               0     100                                                 Lambsquarters       --     100                                                 Persn Speedwell      0     100                                                 Rape                 0      50                                                 Ryegrass             0      30                                                 Sugar beet          60     100                                                 Sunflower            0      60                                                 Wheat (Spring)       0      30                                                 Wheat (Winter)       0      20                                                 Wild buckwheat      25     100                                                 Wild mustard        20      60                                                 Wild oat (1)         0      20                                                 Wild oat (2)         0      40                                                 Wild radish          0      50                                                 Winter Barley        0      20                                                 ______________________________________                                                          COMPOUND                                                      Rate 8 g/ha      1                                                             ______________________________________                                         PREEMERGENCE                                                                   Blackgrass (1)   0                                                             Blackgrass (2)   0                                                             Chickweed        25                                                            Downy brome      0                                                             Field violet     0                                                             Galium (1)       30                                                            Galium (2)       25                                                            Green foxtail    35                                                            Kochia           35                                                            Lambsquarters    --                                                            Persn Speedwell  20                                                            Rape             0                                                             Ryegrass         20                                                            Sugar beet       45                                                            Sunflower        0                                                             Wheat (Spring)   0                                                             Wheat (Winter)   0                                                             Wild buckwheat   30                                                            Wild mustard     20                                                            Wild oat (1)     0                                                             Wild oat (2)     0                                                             Wild radish      0                                                             Winter Barley    0                                                             ______________________________________                                                          COMPOUND                                                      Rate 4 g/ha      9                                                             ______________________________________                                         POSTEMERGENCE                                                                  Blackgrass (1)   30                                                            Blackgrass (2)    0                                                            Chickweed        100                                                           Downy brome      10                                                            Field violet     100                                                           Galium (1)       100                                                           Galium (2)       100                                                           Green foxtail    75                                                            Kochia           100                                                           Lambsquarters    100                                                           Persn Speedwell  100                                                           Rape             50                                                            Ryegrass          0                                                            Sugar beet       100                                                           Sunflower        50                                                            Wheat (Spring)   20                                                            Wheat (Winter)   20                                                            Wild buckwheat   50                                                            Wild mustard     60                                                            Wild oat (1)     10                                                            Wild oat (2)     20                                                            Wild radish      50                                                            Winter Barley    15                                                            ______________________________________                                                          COMPOUND                                                      Rate 2 g/ha      9                                                             ______________________________________                                         POSTEMERGENCE                                                                  Blackgrass (1)   20                                                            Blackgrass (2)    0                                                            Chickweed        100                                                           Downy brome      10                                                            Field violet     50                                                            Galium (1)       100                                                           Galium (2)       40                                                            Green foxtail    40                                                            Kochia           70                                                            Lambsquarters    70                                                            Persn Speedwell  40                                                            Rape              0                                                            Ryegrass          0                                                            Sugar beet       80                                                            Sunflower        --                                                            Wheat (Spring)   20                                                            Wheat (Winter)   20                                                            Wild buckwheat   --                                                            Wild mustard     40                                                            Wild oat (1)     10                                                            Wild oat (2)     10                                                            Wild radish      30                                                            Winter Barley    15                                                            ______________________________________                                    

TEST D

Seeds, rhizomes, or plant parts of alfalfa (Medicago sativa), bermudagrass (Cynodon dactylon), broadleaf signalgrass (Brachiaria plantyphylla), common ragweed (Ambrosia elatior), dallisgrass (Paspalum Dilatatum), goosegrass (Eleusine indica), guineagrass (Panicum maximum), itchgrass (Rottboellia exaltata), johnsongrass (Sorghum halepense), ann bluegrass (Poa annua), large crabgrass (Digitaria sanguinalis), P. J. legume (Pueraria javanica), pitted morningglory (Ipomoea lacunosa), peanuts (Arachis hypogaea), purple nutsedge (Cyperus rotundus), sandbur (Cenchrus echinatus), smooth crabgrass (Digitaria ischaemum), common purslane (Portulaca oleracea), TX panicum (Panicum texanum) and yellow nutsedge (Cyperus esculentus) were planted into greenhouse pots containing greenhouse planting medium.

Each pot contained only one plant species. The test compound was dissolved in a non-phytotoxic solvent and applied preemergence and/or postemergence to the plants.

Preemergence applications were made within one day of planting the seeds or plant parts. Postemergence applications were applied when the plants were in the two to four leaf stage (three to twenty cm).

Test chemicals were dissolved in a non-phytotoxic solvent and applied preemergence and postemergence to the plants. Untreated control plants and treated plants were placed in the greenhouse and visually evaluated for injury at 13 to 21 days after herbicide application.

Plant response ratings, summarized in Table D, are based on a 0 to 100 scale where 0 is no injury and 100 is complete control. A dash (-) response indicates no test result.

                                      TABLE D                                      __________________________________________________________________________                COMPOUND                                                            Rate 1000 g/ha                                                                            8                                                                   __________________________________________________________________________     POSTEMERGENCE                                                                  Alfalfa Var.                                                                              30                                                                  Ann Bluegrass                                                                             30                                                                  Bermudagrass                                                                              60                                                                  Brdlf Sgnlgrass                                                                           70                                                                  Cmn Purslane                                                                              90                                                                  Cmn Ragweed                                                                               --                                                                  Dallisgrass                                                                               60                                                                  Goosegrass 60                                                                  Guineagrass                                                                               20                                                                  Itchgrass  30                                                                  Johnsongrass                                                                              50                                                                  Large Crabgrass                                                                           50                                                                  P J Legume --                                                                  Peanuts    70                                                                  Pit Morninglory                                                                           60                                                                  Purple Nutsedge                                                                           --                                                                  S. Sandbur 60                                                                  Smooth Crabgras                                                                           40                                                                  Texas Panicum                                                                             40                                                                  Yellow Nutsedge                                                                           --                                                                  __________________________________________________________________________                COMPOUND                                                            Rate 500 g/ha                                                                             3                 8  16                                             __________________________________________________________________________     POSTEMERGENCE                                                                  Alfalfa Var.                                                                              100               40 0                                              Ann Bluegrass                                                                             100               40 0                                              Bermudagrass                                                                              100               80 0                                              Brdlf Sgnlgrass                                                                           100               100                                                                               0                                              Cmn Purslane                                                                              100               100                                                                               30                                             Cmn Ragweed                                                                               --                -- 0                                              Dallisgrass                                                                               100               90 0                                              Goosegrass 100               90 0                                              Guineagrass                                                                               100               50 0                                              Itchgrass  100               50 0                                              Johnsongrass                                                                              100               70 0                                              Large Crabgrass                                                                           100               30 0                                              P J Legume --                -- --                                             Peanuts     90               60 20                                             Pit Morninglory                                                                           100               70 0                                              Purple Nutsedge                                                                           --                 0 --                                             S. Sandbur 100               20 0                                              Smooth Crabgras                                                                           100               50 0                                              Texas Panicum                                                                             100               20 --                                             Yellow Nutsedge                                                                           --                 0 --                                             __________________________________________________________________________                           COMPOUND                                                 Rate 500 g/ha         8  16                                                    __________________________________________________________________________     PREEMERGENCE                                                                   Alfalfa Var.           80                                                                               0                                                     Ann Bluegrass         100                                                                               0                                                     Bermudagrass          100                                                                               90                                                    Brdlf Sgnlgrass       100                                                                               0                                                     Cmn Purslane          100                                                                               0                                                     Cmn Ragweed           -- 20                                                    Dallisgrass           100                                                                               90                                                    Goosegrass            100                                                                               80                                                    Guineagrass           100                                                                               100                                                   Itchgrass              80                                                                               0                                                     Johnsongrass          100                                                                               0                                                     Large Crabgrass       100                                                                               90                                                    Peanuts                70                                                                               0                                                     Pit Morninglory        90                                                                               0                                                     Purple Nutsedge        80                                                                               --                                                    S. Sandbur            100                                                                               0                                                     Smooth Crabgras       100                                                                               100                                                   Texas Panicum          90                                                                               --                                                    Yellow Nutsedge        80                                                                               --                                                    __________________________________________________________________________                COMPOUND                                                            Rate 250 g/ha                                                                             1  3  4  5 6 8  9  11 12 13 14                                                                               15 16                                                                               17 18                            __________________________________________________________________________     POSTEMERGENCE                                                                  Alfalfa Var.                                                                              50 100                                                                               60 0 10                                                                               40 100                                                                               100                                                                               0  40 30                                                                               10 10                                                                               0  0                             Ann Bluegrass                                                                             100                                                                               100                                                                               50 0 0 20 -- 20 0  -- --                                                                               -- 0 0  0                             Bermudagrass                                                                              0  100                                                                               60 0 0 40 100                                                                               100                                                                               0  70 0 0  0 0  0                             Brdlf Sgnlgrass                                                                           0  100                                                                               770                                                                               0 0 20 100                                                                               100                                                                               0  10 0 0  0 0  0                             Cmn Purslane                                                                              100                                                                               100                                                                               100                                                                               0 0 100                                                                               100                                                                               100                                                                               90 100                                                                               80                                                                               70 20                                                                               20 20                            Cmn Ragweed                                                                               90 100                                                                               -- --                                                                               --                                                                               -- -- -- -- -- --                                                                               -- 0 100                                                                               100                           Dallisgrass                                                                               50 100                                                                               90 0 0 0  100                                                                               100                                                                               0  70 0 0  0 0  0                             Goosegrass 20 100                                                                               70 0 0 0  100                                                                               100                                                                               0  90 0 0  0 0  0                             Guineagrass                                                                               0  100                                                                               50 0 0 10 100                                                                               100                                                                               0  0  0 0  0 0  0                             Itchgrass  0  100                                                                               50 0 0 0  100                                                                               100                                                                               0  40 0 0  0 0  0                             Johnsongrass                                                                              20 100                                                                               100                                                                               0 0 80 100                                                                               100                                                                               0  90 0 0  0 0  0                             Large Crabgrass                                                                           0  100                                                                               60 0 0 20 100                                                                               100                                                                               0  100                                                                               0 0  0 0  0                             P J Legume 20 100                                                                               -- --                                                                               --                                                                               -- -- -- -- -- --                                                                               -- --                                                                               -- --                            Peanuts    20 100                                                                               50 0 10                                                                               20 80 90 20 50 0 20 0 30 60                            Pit Morninglory                                                                           0  100                                                                               90 0 0 30 100                                                                               100                                                                               0  50 0 0  0 0  30                            Purple Nutsedge                                                                           0  90 0  0 0 0  70 90 -- 0  0 10 --                                                                               0  0                             S. Sandbur 0  100                                                                               60 0 0 0  100                                                                               100                                                                               0  0  0 0  0 0  0                             Smooth Crabgras                                                                           0  100                                                                               60 0 0 0  100                                                                               100                                                                               0  0  0 0  0 0  0                             Texas Panicum                                                                             0  100                                                                               90 0 0 0  -- -- -- -- --                                                                               -- --                                                                               -- --                            Yellow Nutsedge                                                                           0  100                                                                               0  0 0 0  100                                                                               100                                                                               -- 0  0 20 --                                                                               0  0                             PREEMERGENCE                                                                   Alfalfa Var.                                                                              80 100                                                                               100                                                                               0 0 50 100                                                                               100                                                                               100                                                                               0  0 0  0 20 60                            Ann Bluegrass                                                                             20 100                                                                               100                                                                               0 0 70 100                                                                               100                                                                               60 70 0 0  0 0  100                           Bermudagrass                                                                              20 100                                                                               100                                                                               0 0 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               90                                                                               30 40                                                                               30 100                           Brdlf Sgnlgrass                                                                           0  100                                                                               100                                                                               0 0 70 100                                                                               100                                                                               90 0  0 0  0 0  100                           Cmn Purslane                                                                              100                                                                               100                                                                               100                                                                               0 0 100                                                                               100                                                                               100                                                                               100                                                                               60 0 0  0 0  0                             Cmn Ragweed                                                                               100                                                                               100                                                                               -- --                                                                               --                                                                               -- -- -- -- -- --                                                                               -- 0 0  80                            Dallisgrass                                                                               100                                                                               100                                                                               100                                                                               0 0 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               90                                                                               100                                                                               80                                                                               20 100                           Goosegrass 100                                                                               100                                                                               100                                                                               0 0 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               90                                                                               100                                                                               0 90 100                           Guineagrass                                                                               70 100                                                                               100                                                                               0 0 100                                                                               100                                                                               100                                                                               100                                                                               70 0 0  0 60 100                           Itchgrass  0  100                                                                               100                                                                               0 0 60 100                                                                               100                                                                               80 20 0 0  0 0  70                            Johnsongrass                                                                              30 100                                                                               100                                                                               0 0 90 100                                                                               100                                                                               100                                                                               0  0 0  0 0  770                           Large Crabgrass                                                                           100                                                                               100                                                                               100                                                                               0 0 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               90                                                                               80 30                                                                               70 100                           Peanuts    0  100                                                                               40 0 0 10 30 100                                                                               0  10 0 0  0 20 50                            Pit Morninglory                                                                           50 100                                                                               80 0 0 70 100                                                                               100                                                                               60 0  0 0  0 20 60                            Purple Nutsedge                                                                           0  100                                                                               10 0 0 80 50 90 -- 0  0 0  --                                                                               0  0                             S. Sandbur 0  100                                                                               100                                                                               0 0 70 100                                                                               100                                                                               100                                                                               90 0 0  0 0  100                           Smooth Crabgras                                                                           100                                                                               70 100                                                                               0 0 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               30                                                                               100                                                                               80                                                                               70 100                           Texas Panicum                                                                             90 100                                                                               100                                                                               0 0 90 -- -- -- -- --                                                                               -- --                                                                               -- --                            Yellow Nutsedge                                                                           0  90 20 0 0 70 80 90 -- 20 0 0  --                                                                               0  60                            __________________________________________________________________________                COMPOUND                                                            Rate 125 g/ha                                                                             1   2   3   8   9   11  12  13  14 15 16                            __________________________________________________________________________     POSTEMERGENCE                                                                  Alfalfa Var.                                                                              50  70  100 0   100 100 0   0   0  0  10                            Ann Bluegrass                                                                             --  --  100 0   --  0   0   --  -- -- 0                             Bermudagrass                                                                              0   --  100 0   80  100 0   0   0  0  0                             Brdlf Sgnlgrass                                                                           0   0   100 0   100 100 0   0   0  0  0                             Cmn Purslane                                                                              100 100 100 60  100 100 0   100 70 60 20                            Cmn Ragweed                                                                               50  90  100 --  --  --  --  --  -- -- 0                             Dallisgrass                                                                               0   100 100 0   100 100 0   0   0  0  0                             Goosegrass 0   80  100 0   100 100 0   0   0  0  0                             Guineagrass                                                                               0   0   100 0   80  100 0   0   0  0  0                             Itchgrass  0   0   100 0   60  90  0   0   0  0  0                             Johnsongrass                                                                              20  0   100 0   100 100 0   0   0  0  0                             Large Crabgrass                                                                           0   0   100 0   990 100 0   0   0  0  0                             P J Legume 20  80  90  --  --  --  --  --  -- -- --                            Peanuts    10  0   100 20  80  80  0   0   0  0  0                             Pit Morninglory                                                                           0   40  100 30  100 100 0   0   0  0  0                             Purple Nutsedge                                                                           0   0   90  0   60  80  --  0   0  0  --                            S. Sandbur 0   0   100 0   100 100 0   0   0  0  0                             Smooth Crabgras                                                                           0   --  100 0   80  80  0   0   0  0  0                             Texas Panicum                                                                             0   0   100 0   --  --  --  --  -- -- --                            Yellow Nutsedge                                                                           0   0   100 0   100 100 --  0   0  0  --                            PREEMERGENCE                                                                   Alfalfa Var.                                                                              0   50  100 0   100 100 80  0   0  0  0                             Ann Bluegrass                                                                             0   0   100 10  100 100 0   60  0  0  0                             Bermudagrass                                                                              0   30  100 100 100 100 100 100 70 30 0                             Brdlf Sgnlgrass                                                                           0   0   100 10  100 100 0   0   0  0  0                             Cmn Purslane                                                                              50  100 100 90  100 100 30  20  0  0  0                             Cmn Ragweed                                                                               100 100 100 --  --  --  --  --  -- -- 0                             Dallisgrass                                                                               10  30  100 100 100 100 70  100 20 20 0                             Goosegrass 10  90  100 100 100 100 100 100 90 90 0                             Guineagrass                                                                               0   0   100 100 100 100 30  100 0  0  0                             Itchgrass  0   0   100 50  100 100 0   0   0  0  0                             Johnsongrass                                                                              0   0   100 50  100 100 0   30  0  0  0                             Large Crabgrass                                                                           90  0   100 100 100 100 100 100 90 80 0                             Peanuts    0   0   80  0   80  70  0   0   0  0  0                             Pit Morninglory                                                                           0   0   100 0   100 100 50  0   0  0  0                             Purple Nutsedge                                                                           0   70  90  10  10  80  --  0   0  0  --                            S. Sandbur 0   90  100 0   100 100 0   0   0  0  0                             Smooth Crabgras                                                                           20  0   100 100 100 100 90  100 0  0  0                             Texas Panicum                                                                             20  0   100 0   --  --  --  --  -- -- --                            Yellow Nutsedge                                                                           0   0   80  0   30  90  --  0   0  0  --                            __________________________________________________________________________                COMPOUND                                                            Rate 64 g/ha                                                                              3                  11 12                                            __________________________________________________________________________     POSTEMERGENCE                                                                  Alfalfa Var.                                                                               90                60 0                                             Ann Bluegrass                                                                              60                 0 0                                             Bermudagrass                                                                               70                 0 0                                             Brdlf Sgnlgrass                                                                           100                30 0                                             Cmn Purslane                                                                              100                100                                                                               40                                            Cmn Ragweed                                                                               --                 -- --                                            Dallisgrass                                                                               100                 0 0                                             Goosegrass 100                30 0                                             Guineagrass                                                                               100                 0 0                                             Itchgrass   70                 0 0                                             Johnsongrass                                                                              100                40 0                                             Large Crabgrass                                                                           100                 0 0                                             P J Legume --                 -- --                                            Peanuts    100                30 0                                             Pit Morninglory                                                                           100                30 0                                             Purple Nutsedge                                                                            80                -- --                                            S. Sandbur  90                 0 0                                             Smooth Crabgras                                                                            80                 0 0                                             Texas Panicum                                                                             100                -- --                                            Yellow Nutsedge                                                                           100                -- --                                            PREEMERGENCE                                                                   Alfalfa Var.                                                                              100                100                                                                               20                                            Ann Bluegrass                                                                             100                 60                                                                                0                                            Bermudagrass                                                                              100                100                                                                               90                                            Brdlf Sgnlgrass                                                                           100                100                                                                                0                                            Cmn Purslane                                                                              100                100                                                                               80                                            Cmn Ragweed                                                                               --                 -- --                                            Dallisgrass                                                                               100                100                                                                               100                                           Goosegrass 100                100                                                                               100                                           Guineagrass                                                                               100                100                                                                               90                                            Itchgrass  100                100                                                                                0                                            Johnsongrass                                                                              100                100                                                                               50                                            Large Crabgrass                                                                           100                100                                                                               100                                           Peanuts     40                 60                                                                                0                                            Pit Morninglory                                                                           100                100                                                                                0                                            Purple Nutsedge                                                                            80                -- --                                            S. Sandbur 100                100                                                                                0                                            Smooth Crabgras                                                                           100                100                                                                               70                                            Texas Panicum                                                                             100                -- --                                            Yellow Nutsedge                                                                            80                -- --                                            __________________________________________________________________________                            COMPOUND                                                Rate 32 g/ha           3  11                                                   __________________________________________________________________________     POSTEMERGENCE                                                                  Alfalfa Var.           80 30                                                   Ann Bluegrass          50  0                                                   Bermudagrass           70  0                                                   Brdlf Sgnlgrass        90  0                                                   Cmn Purslane           100                                                                               100                                                  Cmn Ragweed            -- --                                                   Dallisgrass            90  0                                                   Goosegrass             80  0                                                   Guineagrass            40  0                                                   Itchgrass              50  0                                                   Johnsongrass           100                                                                               20                                                   Large Crabgrass        20  0                                                   P J Legume             -- --                                                   Peanuts                70 50                                                   Pit Morninglory        100                                                                               50                                                   Purple Nutsedge        20 --                                                   S. Sandbur             20  0                                                   Smooth Crabgras        40  0                                                   Texas Panicum          80 --                                                   Yellow Nutsedge        20 --                                                   PREEMERGENCE                                                                   Alfalfa Var.            70                                                                               100                                                  Ann Bluegrass           90                                                                                30                                                  Bermudagrass           100                                                                               100                                                  Brdlf Sgnlgrass         90                                                                                30                                                  Cmn Purslane           100                                                                               100                                                  Cmn Ragweed            -- --                                                   Dallisgrass            100                                                                               100                                                  Goosegrass             100                                                                               100                                                  Guineagrass            100                                                                                90                                                  Itchgrass              100                                                                                60                                                  Johnsongrass            90                                                                                70                                                  Large Crabgrass        100                                                                               100                                                  Peanuts                 50                                                                                0                                                   Pit Morninglory        100                                                                                20                                                  Purple Nutsedge         60                                                                               --                                                   S. Sandbur             100                                                                                80                                                  Smooth Crabgras        100                                                                               100                                                  Texas Panicum           90                                                                               --                                                   Yellow Nutsedge         70                                                                               --                                                   __________________________________________________________________________

TEST E

Plastic windowsill flats were filled with planting medium and sprayed with the test compounds formulated in a non-phytotoxic spray solution. Treated soil was then placed in plastic bags and shaken thoroughly to incorporate the compounds in the soil. Seedings of cabbage (Early Copenhagen variety) and tomato (Rutgers Select and Ramapo VF FL hybrid varieties) were transplanted into the spiked soil. Untreated or antidote (naphthalic anyhdride) treated corn seeds were also planted into the spiked soil.

Plants were visually rated and compared with the appropriate controls. Injury ratings were based on a scale of 0 to 100 where 0 indicates no effect, 20 indicates minimal effect and 100 indicates complete control. Results are shown in Table E.

                                      TABLE E                                      __________________________________________________________________________             Rate     Tomato                                                                               Tomato                                                                              Corn  Corn                                         COMPOUND                                                                               g/ha                                                                              Cabbage                                                                              Rutgers                                                                              Ramapo                                                                              Untreated                                                                            Treated                                      __________________________________________________________________________                (14 DAT)         (10 DAT)                                           3       4  10    15    15   0     0                                                    8  45    85    75   0     0                                                    16 70    100   100  40    0                                                    32 100   100   100  70    10                                                   64 100   100   100  80    30                                                            (32 DAT)   (28 DAT)                                           3       4  0     0     0    0     0                                                    8  10    100   45   0     0                                                    16 60    100   100  25    0                                                    32 100   100   100  65    40                                                   64 100   100   100  90    70                                                            (14 DAT)   (10 DAT)                                           8       32 0     0     0    0     0                                                    64 0     0     0    0     0                                                    125                                                                               10    0     0    0     0                                                    250                                                                               65    15    5    0     0                                                    500                                                                               60    55    55   0     0                                                             (32 DAT)   (28 DAT)                                           8       32 0     0     0    0     0                                                    64 0     0     0    0     0                                                    125                                                                               0     0     0    0     0                                                    250                                                                               50    0     0    10    0                                                    500                                                                               55    30    20   10    0                                            __________________________________________________________________________

TEST F

Sugarcane varieties CP70-321 and CP70-330 were planted in 15.2 cm plastic pots which were also seeded with large crabgrass (Digitaria sanguinalis) and Lalang (Imperata cylindrica) rhizomes were planted in 20.3 cm plastic pots which also had volunteer fern (Nephrolepis pectinata) plants growing in them. In another test, guineagrass (Panicum maximum), Paspalum conjugatum, Asystasia intrusa and Nephrolepis pectinata plants were grown in planting medium in plastic pots. The plants were treated postemergence with the test compounds formulated in a non-phytotoxic spray solution.

Treated plants were visually rated at the end of the test and compared with the appropriate controls. Injury ratings werebased on a scale of 0 to 100 where 0 indicates no effect, 20 indicates minimal effect and 100 indicates complete control. Results are shownin Table F.

                                      TABLE F                                      __________________________________________________________________________             Rate                                                                              Sugarcane  Large                                                    COMPOUND                                                                               g/ha                                                                              CP70-321                                                                             CP70-330                                                                            Crabgrass                                                                             Lalang                                                                             Fern                                          __________________________________________________________________________      3      32 0     0    50     30  0                                                     64 0     0    60     30  0                                                     125                                                                               0     0    85     30  0                                              8      500                                                                               0     0     0      0  0                                                     1000                                                                              0     0    30     30  0                                                     2000                                                                              0     0    60     60  20                                            __________________________________________________________________________             Rate      Paspalum                                                                              Asystasia                                                                           Nephrolepis                                      COMPOUND                                                                               g/ha                                                                              Guineagrass                                                                           Conjugalum                                                                            intrusa                                                                             pectinate                                        __________________________________________________________________________     11      64 40     0      45   0                                                        125                                                                               50     0      40   0                                                        250                                                                               75     30     50   0                                                        500                                                                               80     45     60   0                                                12      64  0     0       0   0                                                        125                                                                                0     0       0   0                                                        250                                                                               30     0       0   0                                                        500                                                                               30     0       0   0                                                __________________________________________________________________________

TEST G

Sugarcane (Saccharum officinarum), purple nutsedge (Cyperus rotundus), Brachiaria decumbens and Brachiaria plantaginea were planted in fiberglass trays. Plants were treated postemergence with the test compounds formulated in a non-phytotoxic spray solution.

Treated plants were visually rated and compared with appropriate controls. Injury ratings were based on a scale of 0 to 100 where 0 indicates no effect, 20 indicates minimal effect and 100 indicates complete control. Results are shown in Table G.

                  TABLE G                                                          ______________________________________                                         COM-   Rate             Purple Brachiaria                                                                             Brachiaria                              POUND  g/ha   Sugarcane nutsedge                                                                              decumbens                                                                              plantaginea                             ______________________________________                                          8     500    0         20     90      60                                             1000   0         30     100     100                                            2000   20        60     100     100                                     11     32     0          0      0       0                                             64     10         0     70      60                                             125    30         0     90      90                                      12     64     0          0      0       0                                             125    0          0      0       0                                      ______________________________________                                    

TEST H

Pineapple (Ananas comosus), guineagrass (Panicum maximum) and swollen fingergrass (Chloris inflata) were planted in potting medium. Plants were treated postemergence with the test compound formulated in a non-phytotoxic spray solution.

Treatments were visually rated and compared with the appropriate controls. Injury ratings were based on a scale of 0 to 100 where 0 indicates no effect, 20 indicates minimal effect and 100 indicates complete control. Results are shown in Table H.

                  TABLE H                                                          ______________________________________                                                   Rate                       Swollen                                   COMPOUND  g/ha    Pineapple Guineagrass                                                                             fingergrass                               ______________________________________                                         8         250     0          0       0                                                   500     0          0       0                                                   1000    0         30       0                                                   2000    0         40       80                                        ______________________________________                                    

TEST I

Cuttings of turf species Zoysia spp., and St. Augustine (Stenotaphrum secundatum) were planted in 11.4 cm plastic pots filled with planting medium. Smooth crabgrass (Digitaria ischaemum) and large crabgrass (Digitaria sanguinalis) seeds were also planted and grown in 11.4 cm plastic pots. Plants were treated postemergence with the test compounds.

Treatments were visually rated at the end of the test and compared with the appropriate controls. Injury ratings were based on a scale of 0 to 100 where 0 indicates no effect, 20 indicates minimal effect and 100 indicates complete control. Results are shown in Table I.

                  TABLE I                                                          ______________________________________                                         COM-   Rate            St.     Smooth  Large                                   POUND  g/ha    Zoysia  Augustine                                                                              Crabgrass                                                                              Crabgrass                               ______________________________________                                         3      4       0       0        0       0                                             8       0       0        0       0                                             16      0       0       10      40                                             32      0       0       10      50                                             64      0       0       30      70                                      8      64      0       0        0       0                                             125     30      0        0      50                                             250     50      20      20      90                                             500     50      20      40      90                                      ______________________________________                                    

TEST J

Fifteen different soybean varieties including Williams, W-20 and the Asgrow varieties A3242, A3935, A4715, A5979, A3322, A4009, A4906, A6297, A3205, A3733, A4595, A5403 and A6961 were planted separately in plastic pots filled with planting medium. The pots were tested preemergence with the test chemicals formulated in a non-phytotoxic spray solution.

Plants were visually rated at the end of the test and compared with the appropriate controls. Injury ratings were based on a scale of 0 to 100 where 0 indicates no effect, 20 indicates minimal effect and 100 indicates complete control. Results are shown in Table J.

                                      TABLE J                                      __________________________________________________________________________             Rate                                                                   COMPOUND                                                                               g/ha                                                                              Williams                                                                            W20                                                                               A3205                                                                              A3242                                                                              A3322                                                                              A3733                                                                              A3935                                                                              A4009                                   __________________________________________________________________________     11      16 20   20 20  20  20  30  20  40                                              32 60   50 50  60  50  50  70  70                                              64 90   90 80  90  90  90  90  90                                              125                                                                               100  100                                                                               100 100 100 100 100 100                                     __________________________________________________________________________             Rate                                                                   COMPOUND                                                                               g/ha                                                                              A4595                                                                               A4715                                                                              A4906                                                                               A5403                                                                              A5979                                                                               A6297                                                                              A6961                                    __________________________________________________________________________     11      16 20   30  60   50  40   60  20                                               32 60   70  60   60  70   100 100                                              64 90   90  90   90  90   90  90                                               125                                                                               100  100 100  100 100  100 100                                      12      16 0    0   0    0   0    0   0                                                32 0    0   0    0   0    0   0                                                64 0    0   0    0   0    0   0                                                125                                                                               20   20  20   20  20   20  20                                       __________________________________________________________________________

TEST K

Corn, soybean, tomato, morningglory, different nightshade varieties [Solanum nigrum (entire and serrated leaf), S. nigrum subsp. nigrum, S. interius, S. ptycanthus (green berries and black berries), S. nigrum subsp. schultesii and triazine-tolerant nightshade] seeds and potato eye cuttings were planted in separate 11.4 cm plastic pots filled with planting medium. The pots were sprayed preemergence with the test chemicals formulated in a non-phytotoxic spray solvent.

Plants were visually rated at the end of the test and compared with appropriate controls. Injury ratings were based on a scale of 0 to 100 where 0 indicates no effect, 20 indicates minimal effect and 100 indicates complete control. Results are shown in Table K.

                                      TABLE K                                      __________________________________________________________________________                                    Triazine                                                Rate                   Tolerant                                        COMPOUND                                                                               g/ha                                                                              Corn                                                                              Soybean                                                                             Tomato                                                                              Morningglory                                                                          Nightshade                                                                           Potato                                    __________________________________________________________________________     11      2  0  0    0    0      0     0                                                 4  30 20   20   40     0     20                                        12      16 0  0    0    0      0     0                                                 32 0  0    0    20     --    0                                                 64 0  0    20   40     70    20                                                125                                                                               0  0    60   50     100   60                                        __________________________________________________________________________                S. Nigrum                                                                            S. Nigrum                                                                            S. Nigrum   S. Ptyanthus                                        Rate                                                                              Entire                                                                               Serrated                                                                             Subs.       Green                                       COMPOUND                                                                               g/ha                                                                              Leaf  Leaf  Nigrum                                                                               S. Interius                                                                          Berries                                     __________________________________________________________________________     11      2  0     0     0     0     0                                                   4  0     0     0     0     0                                           12      16 0     0     0     0     0                                                   32 0     30    20    70    40                                                  64 0     70    60    100   100                                                 125                                                                               60    100   80    100   100                                         __________________________________________________________________________             Rate                                                                   COMPOUND                                                                               g/ha                                                                              S. Ptyanthus Black Berries                                                                  S. Nigrum Sub. Schultesii                              __________________________________________________________________________     11      2  0            0                                                              4  0            0                                                      12      16 0            0                                                              32 0            0                                                              64 50           20                                                             125                                                                               70           60                                                     __________________________________________________________________________

TEST L

Rooted cuttings of rough lemon (Citrus sp.) were planted in 30 liter plastic pots. These pots were also seeded with guineagrass (Panicum maximum), sandbur (Cenchrus enchinatus) and pigweed (Amaranthus viridis). The weeds were cutback many times to simulate mowing and the citrus plant also trimmed.

The citrus was sprayed to simulate field type post-directed herbicide application while the weeds were treated postemergence over the top with the test compounds formulated in a non-phytotoxic spray solvent. In a separate test, loblolly pine seedlings were also sprayed over-the-top with the test compounds formulated in a non-phytotoxic spray solvent. Treated plants were visually rated and compared with appropriate controls. The injury ratings are based on the scale of 0 to 100 where 0 indicates no effect, 20 indicates minimal effect and 100 indicates complete control. The results are shown in Tables L1 and L2. The differences in results may be due to the fact that the tests were conducted using plants at different stages of growth.

                  TABLE L1                                                         ______________________________________                                                      COMPOUND                                                          Rate (500 g/ha)                                                                               1          2      3                                             ______________________________________                                         POST-DIRECTED                                                                  Rough Lemon    0          0      0                                             ______________________________________                                                      COMPOUND                                                          Rate (50 g/ha) 1          2      3                                             ______________________________________                                         OVER-THE-TOP                                                                   Guineagrass    0          0      70                                            Pigweed        0          0      70                                            Sandbur        0          0      0                                             ______________________________________                                                      COMPOUND                                                          Rate (250 g/ha)                                                                               1          2      3                                             ______________________________________                                         POST-DIRECTED                                                                  Rough Lemon    0          0      0                                             OVER-THE-TOP                                                                   Guineagrass    0          0      30                                            Pigweed        0          0      40                                            Sandbur        0          0      0                                             ______________________________________                                                      COMPOUND                                                          Rate (125 g/ha)                                                                               1          2      3                                             ______________________________________                                         POST-DIRECTED                                                                  Rough Lemon    0          0      0                                             OVER-THE-TOP                                                                   Guineagrass    0          0      30                                            Pigweed        0          0      0                                             Sandbur        0          0      0                                             ______________________________________                                    

                  TABLE L2                                                         ______________________________________                                                       COMPOUND                                                         Rate (250 g/ha) 3      5        6   8                                          ______________________________________                                         POST-DIRECTED                                                                  Rough Lemon      30*   0        0    0                                         OVER-THE-TOP                                                                   Loblolly pine   70     0        0    0                                         Guineagrass     70     0        0   20                                         Pigweed         20     0        0   40                                         Sandbur         60     0        0   30                                         ______________________________________                                                       COMPOUND                                                         Rate (125 g/ha)                                                                              8                                                                ______________________________________                                         POST-DIRECTED                                                                  Rough Lemon   0                                                                OVER-THE-TOP                                                                   Loblolly pine 0                                                                Guineagrass   10                                                               Pigweed       30                                                               Sandbur       10                                                               ______________________________________                                          *Compound contacted leaves after treatment.                               

What is claimed is:
 1. A method for controlling the growth of undesired vegetation in plantation crops selected from the group consisting of citrus, sugarcane, coffee, banana, oil palm, loblolly pine, rubber, cocoa, grapes, plantain, pineapple, fruit trees and nut trees which comprises applying to the locus of the crop an herbicidally effective amount of a compound of Formula I ##STR418## A is O or S; R¹ is C₁ -C₄ alkyl optionally substituted with one or more halogen, OR⁵, SR⁶ or CN; C₃ -C₆ alkenyl or C₃ -C₆ alkynyl, each optionally substituted with 1-3 halogen atoms; formyl; or C₂ -C₆ alkanoyl;R² is H, isopropyl, allyl, propargyl, CH(CH₃)C≡CH, benzyl, CHR⁷ CO₂ R⁸ or may be taken together with Z; R³ is C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or N(CH₃)₂ ; R⁴ is H or halogen; R⁵ and R⁶ are independently H or C₁ -C₃ alkyl; R⁷ and R⁸ are independently C₁ -C₂ alkyl; X is Cl or Br; Y is F or Cl; Z is H or may be taken together with R² as --CH₂ CHR⁹ such that the linking A atom is attached to the methine carbon; R⁹ is C₁ -C₃ alkyl, C₁ -C₃ haloalkyl, cyclopropyl, vinyl, C₂ alkynyl, CN, C(O)R¹⁰, CO₂ R¹⁰, CONR¹⁰ R¹¹, CR¹² R¹³ C(O)R¹⁰, CR¹² R¹³ CO₂ R¹⁰, CR¹² R¹³ CONR¹⁰ R¹¹, CHR¹² OH, CHR¹² OC(O)R¹⁰ or CHR¹² OC(O)NR¹⁰ R¹¹ ; and R¹⁰, R¹¹, R¹² and R¹³ are independently H or C₁ -C₃ alkyl.
 2. The method of claim 1, whereinR¹ is C₁ -C₃ alkyl optionally substituted with 1 to 3 F atoms or Cl atoms, O(C₁ -C₂ alkyl), S(C₁ -C₂ alkyl ) or CN; C₃ -C₄ alkenyl optionally substituted with 1 to 3 F atoms or Cl atoms; C₃ -C₄ alkynyl; or C₂ -C₃ alkanoyl; R² is H, isopropyl, allyl, propargyl, CH(CH₃)C≡CH, CHR⁷ CO₂ R⁸ or may be taken together with Z; R³ is C₁ -C₂ alkyl, C₁ -C₂ haloalkyl or N(CH₃)₂ ; R⁴ is M, F, Cl or Br; and X is Cl.
 3. The method of claim 2, whereinR¹ is CH₃ optionally substituted with 1 to 3 F atoms or Cl atoms; CH₂ CN; allyl; or propargyl; R³ is CF₃ ; and R⁴ is H.
 4. The method of claim 3, whereinR⁹ is CH₃ ; and A is O.
 5. The method of claim 4, wherein the compound of Formula I is3-[4-chloro-2-fluoro-5-[(2-propynyl)oxy]-phenyl]-1-methyl-6-(trifluoromethyl)-2,4-(1H,3H) -pyrimidinedione; or 3-[4-chloro-2-fluoro-5-(2-propenyloxy)-phenyl]-1-methyl-6-(trifluoromethyl)-2,4-(1H,3H) -pyrimidinedione; or 3-(5,7-dichloro-2,3-dihydro-2-methyl-4-benzofuranyl)-1-methyl-6-(trifluoromethyl)-2,4-(1H,3H)-pyrimidinedione; or 3-(7-choro-5-fluoro-2,3-dihydro-2-methyl-4-benzofuranyl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H) -pyrimidinedione.
 6. The method of claim 1, wherein the compound of Formula I is applied in combination with at least one of the following: surfactant, solid or liquid diluent.
 7. The method of claim 1 wherein the plantation crop is citrus.
 8. A compound of Formula II ##STR419## wherein A is O or S;R¹ is C₁ -C₄ alkyl optionally substituted with one or more halogen, OR⁵, SR⁶ or CN; C₃ -C₆ alkenyl or C₃ -C₆ alkynyl, each optionally substituted with 1-3 halogen atoms; formyl; or C₂ -C₆ alkanoyl; R² is H, isopropyl, allyl, propargyl, CH(CH₃)C≡CH, benzyl, CHR⁷ CO₂ R⁸ or may be taken together with Z; R³ is C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or N(CH₃)₂ ; R⁴ is H or halogen; R⁵ and R⁶ are independently H or C₁ -C₃ alkyl; R⁷ and R⁸ are independently C₁ -C₂ alkyl; X is Cl or Br; Y is F or Cl; Z is H or may be taken together with R² as --CH₂ CHR⁹ such that the linking A atom is attached to the methine carbon; R⁹ is C₁ -C₃ alkyl, C₁ -C₃ haloalkyl, cyclopropyl, vinyl, C₂ alkynyl, CN, C(O)R¹⁰, CO₂ R¹⁰, CONR¹⁰ R¹¹, CR¹² R¹³ C(O)R¹⁰, CR¹² R¹³ CO₂ R¹⁰, CR¹² R¹³ CONR¹⁰ R¹¹, CHR¹² OH, CHR¹² OC(O)R¹⁰ or CHR¹² OC(O)NR¹⁰ R¹¹ ; and R¹⁰, R¹¹, R¹² and R¹³ are independently H or C₁ -C₃ alkyl; provided that1) in compounds of Formula II, when R¹ is C₁ -C₄ alkyl optionally substituted with halogen, OR⁵ or CN; C₃ -C₄ alkenyl; formyl; or C₂ -C₆ alkanoyl; R³ is C₁ -C₄ haloalkyl; and R⁵ is C₁ -C₃ alkyl; then R² is benzyl or taken together with Z; 2) in compounds of Formula II, when R¹ is CH₂ OH or C₁ -C₃ alkyl optionally substituted with halogen; R³ is C₁ -C₄ haloalkyl; and A is S; then R² is taken together with Z; 4) in compounds of Formula II, when R¹ is C₁ -C₄ alkyl optionally substituted with halogen; formyl; or C₂ -C₆ alkanoyl; then R² is taken together with Z.
 9. A compound of claim 8 whereinR¹ is C₁ -C₃ alkyl optionally substituted with 1 to 3 F atoms or Cl atoms, O(C₁ -C₂ alkyl), S (C₁ -C₂ alkyl) or CN; C₃ -C₄ alkenyl optionally substituted with 1 to 3 F atoms or Cl atoms; C₃ -C₄ alkynyl; or C₂ -C₃ alkanoyl; R² is H, isopropyl, allyl, propargyl, CH(CH₃)C≡CH, CHR⁷ CO₂ R⁸ or may be taken together with Z; R³ is C₁ -C₂ alkyl, C₁ -C₂ haloalkyl or N(CH₃)₂ ; R⁴ is H, F, Cl or Br; and X is Cl.
 10. A compound of claim 9 whereinR¹ is CH₃ optionally substituted with 1 to 3 F atoms or Cl atoms; CH₂ CN; allyl; or propargyl; R³ is CF₃ ; and R₄ is H.
 11. A compound of claim 10 whereinR⁹ is CH₃ ; and A is O.
 12. A compound of claim 8 wherein the compound is3-(5,7-dichloro-2,3-dihydro-2-methyl-4-benzofuranyl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione; or 3-(7-choro-5-fluoro-2,3-dihydro-2-methyl-4-benzofuranyl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione.
 13. A method for controlling the growth of undesired vegetation in plantation crops selected from the group consisting of citrus, sugarcane, coffee, banana, oil palm, loblolly pine, rubber, cocoa, grapes, plantain, pineapple, fruit trees and nut trees which comprises applying to the locus of the crop to be protected an effective amount of a compound of claim 8, 9, 10 or
 11. 14. A method for controlling the growth of undesired vegetation in plantation crops selected from the group consisting of citrus, sugarcane, coffee, banana, oil palm, loblolly pine, rubber, cocoa, grapes, plantain, pineapple, fruit trees and nut trees which comprises applying to the locus of the crop to be protected an effective amount of a compound of claim
 12. 15. A method for controlling the growth of undesired vegetation in plantation crops selected from the group consisting of citrus, sugarcane, coffee, banana, oil palm, loblolly pine, rubber, cocoa, grapes, plantain, pineapple, fruit trees and nut trees which comprises applying to the locus of the crop to be protected an effective amount of a composition which comprises an effective amount of a compound of claim 8, 9, 10 or 11, and at least one of the following: surfactant, solid or liquid diluent.
 16. A method for controlling the growth of undesired vegetation in plantation crops selected from the group consisting of citrus, sugarcane, coffee, banana, oil palm, loblolly pine, rubber, cocoa, grapes, plantain, pineapple, fruit trees and nut trees which comprises applying to the locus of the crop to be protected an effective amount of a composition which comprises an effective amount of a compound of claim 12, and at least one of the following: surfactant, solid or liquid diluent. 